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Triethylamine → N-({4-[(2R,3R)-3-{[2-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-3-methyl-D-valine

HRID 603899
Notes
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Reaction equation

HRID 603899 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:11](=[O:12])[C@H:10]([S:13]SC3C([N+]([O-])=O)=CC=CN=3)[C@H:9]2[C:24]2[CH:46]=[CH:45][C:27]([O:28][CH2:29][C:30]([NH:32][CH2:33][C:34]([NH:36][C@@H:37]([C:42]([OH:44])=[O:43])[C:38]([CH3:41])([CH3:40])[CH3:39])=[O:35])=[O:31])=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.Br[CH2:74][C:75]([C:77]1[CH:86]=[CH:85][C:80]2[O:81][CH2:82][CH2:83][O:84][C:79]=2[CH:78]=1)=[O:76].[BH4-].[Na+]>CC(C)=O.O.ClCCl>[O:81]1[C:80]2[CH:85]=[CH:86][C:77]([CH:75]([OH:76])[CH2:74][S:13][C@H:10]3[C:11](=[O:12])[N:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[C@@H:9]3[C:24]3[CH:25]=[CH:26][C:27]([O:28][CH2:29][C:30]([NH:32][CH2:33][C:34]([NH:36][C@@H:37]([C:42]([OH:44])=[O:43])[C:38]([CH3:39])([CH3:41])[CH3:40])=[O:35])=[O:31])=[CH:45][CH:46]=3)=[CH:78][C:79]=2[O:84][CH2:83][CH2:82]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 27761712-Bromo-1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethan-1-oneHCID 4311764Sodium borohydrideHCID 86643073N-[(4-{(2R,3R)-1-(4-fluorophenyl)-3-[(3-nitropyridin-2-yl)dithio]-4-oxoazetidin-2-yl}phenoxy)acetyl]glycyl-3-methyl-D-valine

Product 1

HCID 67271359
N-({4-[(2R,3R)-3-{[2-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-3-methyl-D-valine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a solution of N-[(4-{(2R,3R)-1-(4-fluorophenyl)-3-[(3-nitropyridin-2-yl)dithio]-4-oxoazetidin-2-yl}phenoxy)acetyl]glycyl-3-methyl-D-valine (0.030 g, 0.045 mmol) in acetone/water (2/0.5 ml) was added triphenylphosphine (0.012 g, 0.045 mmol). After 30 minutes the solvent was evaporated and to the residue was added dichloromethane (2 ml) and triethylamine (0.018 g, 0.179 mmol) followed by the addition of 2-bromo-1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethanone (0.029 g, 0.112 mmol). After 10 minutes the reaction was quenched by the addition of water (1 ml) followed by concentration of the mixture. MeOH (2 ml) was added followed by the addition of sodium borohydride (0.017 g, 0.447 mmol). Full conversion to the corresponding alcohol was achieved within 5 minutes. The reaction was quenched by the addition of 0.1M NH4OAc buffer (1 ml). Preparative HPLC of the mixture using an eluent of 20-45% CH3CN in 0.1M NH4OAc buffer followed by freeze drying of pure fractions afforded the desired compound. m/z: 694.7 (M−1). 1H NMR [(CD3)2SO), 400 MHz] δ 0.89 (s, 9H), 2.78-2.89 (m, 2H), 3.82 (d, 2H), 4.05-4.28 (m, 6H), 4.51 (s, 2H), 4.55-4.61 (m, 1H), 5.01-5.03 (m, 1H), 6.72-7.37 (m, 11H), 7.81-7.87 (m, 1H), 8.25 (t, 1H).

Workup

  1. customAfter 30 minutes the solvent was evaporated and to the residue
  2. customAfter 10 minutes the reaction was quenched by the addition of water (1 ml)
  3. additionMeOH (2 ml) was added
  4. customThe reaction was quenched by the addition of 0.1M NH4OAc buffer (1 ml)
  5. customdrying of pure fractions

Sources & evidence

ORD record
ord-22d0db401233491b897fb65be36fddd8
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07906502B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes