HCID 11386534, compound → HCID 11156625, compound

HRID 900338Notes

Reaction equation

HRID 900338 reaction equation
B1([O-])OO1.[OH2:5].O.O.O.[Na+].[C:10]([O:14][C:15]([NH:17][C@@H:18]([CH2:22][S:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][C:34]([N:37]3[C:45]4[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=4)[CH:39]=[CH:38]3)=[CH:33][CH:32]=2)=[CH:27][CH:26]=1)[C:19]([OH:21])=[O:20])=[O:16])([CH3:13])([CH3:12])[CH3:11]>C(O)(=O)C.C(OCC)(=O)C>[C:10]([O:14][C:15]([NH:17][C@@H:18]([CH2:22][S:23]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:32]=[CH:33][C:34]([N:37]3[C:45]4[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=4)[CH:39]=[CH:38]3)=[CH:35][CH:36]=2)=[CH:27][CH:26]=1)=[O:5])[C:19]([OH:21])=[O:20])=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 2

HCID 11386534HCID 11386534, compoundHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

Product 1

HCID 11156625HCID 11156625, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

Sodium perborate tetrahydrate (151 mg, 0.95 mmol) was added as a solid to a stirred solution of (2R)-tert-Butoxycarbonylamino-3-(4′-indol-1-ylbiphen-4-ylmethylsulfanyl)-propionic acid (380 mg, 0.76 mmol) in acetic acid (10 mL) at 40° C. This solution was stirred at 40° C. for 2 hours (HPLC control) and then diluted with ethyl acetate (50 mL), washed with water, brine (2×), dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by trituration of the product with diethyl ether afforded the title compound as a 2:1 mix of diastereoisomers as an off-white solid (372 mg, 95%): mp. 169-170° C. Rf 0.65 (20% methanol in dichloromethane). 1H NMR (DMSO-d6, 300 MHz): δ 7.88 (2H, d, J=8 Hz, Ar—H), 7.62-7.78 (7H, m, Ar—H), 7.44 (2H, d, J=8 Hz, Ar—H), 7.36 (1H, d, J=8 Hz, NH), 7.11-7.22 (2H, m, Ar—H), 6.72 (1H, d, J=3.5 Hz, Ar—H), 4.06-4.26 (3H, m, CHN+PhCH2), 2.96-3.04 (2H, m, CH2CHN), 1.39 (3H, s, CMe3, minor isomer), 1.36 (6H, s, CMe3, major isomer), ESI-LCMS e/z calcd for C29H30N2O5S: 518.631, found 519 (M+H)+, 541 (M+Na)+.

Workup

  1. washwashed with water, brine (2×)
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by trituration of the product with diethyl ether

Sources & evidence

ORD record
ord-291bd240da144b1fb10c2a5a95a1fa66
Source dataset
uspto-grants-2008_04
Patent number
US07358248B2

Reaction notes

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