Triethylamine → (4-phenylphenyl)-methyl-N-[(2R*,3R*)-2-ethyl-4-oxo-oxetan-3-yl]-carbamate

HRID 530549Notes

Reaction equation

HRID 530549 reaction equation
O[C@H](CC)[C@@H](N([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)C(OC)=O)C(O)=O.O[C@@H:27]([CH2:49][CH3:50])[C@@H:28]([N:32]([C:37]1C=CC(C2C=CC=CC=2)=CC=1)[C:33]([O:35]C)=[O:34])[C:29]([OH:31])=[O:30].CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[C:18]1([C:15]2[CH:14]=[CH:13][C:12]([O:35][C:33](=[O:34])[N:32]([CH3:37])[C@H:28]3[C:29](=[O:31])[O:30][C@@H:27]3[CH2:49][CH3:50])=[CH:17][CH:16]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86699986(2R*,3S*)-3-hydroxy-2-[(4-phenylphenyl)-methoxycarbonylamino]-pentanoic acidHCID 86699992(2R*,3R*)-3-hydroxy-2-[(4-phenylphenyl)-methoxycarbonylamino]-pentanoic acid

Product 1

HCID 86699991(4-phenylphenyl)-methyl-N-[(2R*,3R*)-2-ethyl-4-oxo-oxetan-3-yl]-carbamateYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Under nitrogen atmosphere, to a stirred mixture of (2R*,3R*)-3-hydroxy-2-[(4-phenylphenyl)-methoxycarbonylamino]-pentanoic acid and (2R*,3S*)-3-hydroxy-2-[(4-phenylphenyl)-methoxycarbonylamino]-pentanoic acid (0.193 g, 0.56 mmol) in dry CH2Cl2 (25.0 mL), at 0° C., Et3N (0.235 mL, 1.69 mmol) and subsequently TBTU (0.217 g, 0.67 mmol) were added. The mixture was left stirring at 0° C. for 1 h and at rt for 15 h. The organics were then removed under reduced pressure, and the resulting crude product purified by column chromatography, using a Teledyne ISCO apparatus, eluting with Cy/AcOEt (from 90:10 to 80:20) to afford the pure title compound (0.089 g, 57%), as pure anti diastereoisomer, as white solid. MS (ESI) m/z: 343 [M−NH4]+; (ESI) m/z: 324 [M−H]−. 1H NMR (DMSO-d6) δ 0.92 (t, J=7.38 Hz, 3H), 1.68-1.94 (m, 2H), 4.49-4.60 (m, 1H), 4.76 (dd, J=4.32, 8.08 Hz, 1H), 5.12 (s, 2H), 7.33-7.42 (m, 1H), 7.42-7.53 (m, 4H), 7.62-7.76 (m, 4H), 8.25 (d, J=8.09 Hz, 1H).

Workup

  1. waitThe mixture was left
  2. customThe organics were then removed under reduced pressure
  3. customthe resulting crude product purified by column chromatography
  4. washeluting with Cy/AcOEt (from 90:10 to 80:20)

Sources & evidence

ORD record
ord-886e4ad0b842472e8c95ce54c03ef160
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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