Water → HCID 68792808, compound

HRID 1366310Notes

Reaction equation

HRID 1366310 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C@@H:10]([OH:51])[CH2:11][S:12][C@H:13]3[C:16](=[O:17])[N:15]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)[C@@H:14]3[C:25]3[CH:50]=[CH:49][C:28]([O:29][CH2:30][C:31]([NH:33][CH2:34][C:35]([NH:37][C@H:38]([C:46]([OH:48])=[O:47])[CH2:39][CH2:40][CH2:41][CH2:42][N:43]([CH3:45])[CH3:44])=[O:36])=[O:32])=[CH:27][CH:26]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1.O.C([O-])(=O)C.[NH4+]>CC#N.FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.[Sc+3]>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([OH:51])[CH2:11][S:12][C@H:13]3[C:16](=[O:17])[N:15]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)[C@@H:14]3[C:25]3[CH:26]=[CH:27][C:28]([O:29][CH2:30][C:31]([NH:33][CH2:34][C:35]([NH:37][C@H:38]([C:46]([OH:48])=[O:47])[CH2:39][CH2:40][CH2:41][CH2:42][N:43]([CH3:44])[CH3:45])=[O:36])=[O:32])=[CH:49][CH:50]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 962Water3×HCID 517165Ammonium AcetateHCID 68790431HCID 68790431, compound

Product 1

HCID 68792808HCID 68792808, compound

Reagents, catalysts & solvents 2

HCID 2734571Scandium(III) triflateCatalyst2×HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-({4-[(2R,3R)-3-{[(2R)-2-(2,3-dihydro-1-benzofuran-5-yl)-2-hydroxyethyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetyl)glycyl-N6,N6-dimethyl-L-lysine (11.0 mg, 0.013 mmol) in MeCN (1 ml) were added scandium tris(trifluoromethanesulfonate) (0.5 mg, 0.00102 mmol) and water (2 μl, 0.131 mmol). The reaction mixture was stirred for 3 hours. Additional Sc(OTf)3 (0.7 mg, 0.00142 mmol) and water (2 μl, 0.131 mmol) were added and the mixture was stirred for 1 hour. Additional Sscandium tris(trifluoromethanesulfonate) (6.0 mg, 0.01219 mmol)) and water (4 μl, 0.262) were added and the reaction mixture was stirred for 1 hour. Ammonium acetate buffer (0.1M, 1 ml) was added. The resulting solution was purified with preparative HPLC on a C8 column, UV 235/285 nm. A gradient from 20 to 43% MeCN was used as eluent. The pure fractions were collected and most of the MeCN was removed under reduced pressure. The residue was lyophilised to give the title compound. H-NMR (500 MHz, DMSO-d6): 1.21-1.31 (m, 2H), 1.33-1.44 (m, 2H), 1.51-1.60 (m, 1H), 1.63-1.71 (m, 1H), 2.16 (s, 6H), 2.25 (bs, 2H), 2.81-2.94 (m, 2H), 3.01-3.15 (m, 2H), 3.78 (d, 2H), 4.07 (bs, 1H), 4.25 (d, 0.5H) 4.26 (d, 0.5H), 4.44-4.50 (m, 2H), 4.52 (s, 2H), 4.59-4.66 (m, 1H), 5.01-5.05 (b, 1H), 6.64 (dd, 1H), 6.97-7.02 (m, 3H), 7.11-7.18 (m, 3H), 7.21-7.26 (m, 2H), 7.37 (d, 2H), 7.98 (bs, 1H), 8.26 (t, 1H). M/z: 721.40 (M−1)

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. stirringthe reaction mixture was stirred for 1 hour
  3. customThe resulting solution was purified with preparative HPLC on a C8 column, UV 235/285 nm
  4. customThe pure fractions were collected and most of the MeCN
  5. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-d7e3b770722b4c23ac2a847eb66d88ed
Source dataset
uspto-grants-2011_02
Patent number
US07893048B2

Reaction notes

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