HCID 11365072, compound → HCID 59696206, compound

HRID 1782638Notes

Reaction equation

HRID 1782638 reaction equation
B1([O-])OO1.[OH2:5].O.O.O.[Na+].[N:10]1([C:19]2[CH:50]=[CH:49][C:22]([C:23]3[CH:28]=[CH:27][C:26]([CH2:29][S:30][CH2:31][C@H:32]([NH:36][C:37](=[O:48])[CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[C:41]([N+:45]([O-:47])=[O:46])[CH:40]=4)[C:33]([OH:35])=[O:34])=[CH:25][CH:24]=3)=[CH:21][CH:20]=2)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11]1>C(O)(=O)C.C(OCC)(=O)C>[N:10]1([C:19]2[CH:20]=[CH:21][C:22]([C:23]3[CH:28]=[CH:27][C:26]([CH2:29][S:30]([CH2:31][C@H:32]([NH:36][C:37](=[O:48])[CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[C:41]([N+:45]([O-:47])=[O:46])[CH:40]=4)[C:33]([OH:35])=[O:34])=[O:5])=[CH:25][CH:24]=3)=[CH:49][CH:50]=2)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11]1

Participants

5

Reactant 2

HCID 11365072HCID 11365072, compoundHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

Product 1

HCID 59696206HCID 59696206, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

Sodium perborate tetrahydrate (97 mg, 0.63 mmol) was added as a solid to a stirred solution of (2R)-3-(4′-Indol-1-ylbiphen-4-ylmethylsulfanyl)-2-[2-(3-nitrophenyl)-acetylamino]-propionic acid (330 mg, 0.58 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 light brown solid (206 mg, 61%): mp. 197-198° C. Rf 0.15 (15% methanol in dichloromethane): 1H NMR (DMSO-d6, 300 MHz) δ 8.46 (1H, d, J=8 Hz, NH), 8.18 (1H, t, J=2 Hz, Ar—H), 8.08 (1H, ddd, J=8, 2, 1 Hz, Ar—H), 7.87 (2H, d, J=8 Hz, Ar—H), 7.72 (2H, d, J=8 Hz, Ar—H), 7.54-7.69 (7H, m, Ar—H), 7.35 (2H, d, J=8 Hz, Ar—H), 7.21 (1H, td, J=7, 2 Hz, Ar—H), 7.14 (1H, td, J=7, 2 Hz, Ar—H), 6.71 (1H, d, J=3 Hz, Ar—H), 4.36 (1H, m, CHN), 4.20 (1H, d, J=13 Hz, PhCHHS), 3.84 (1H, d, J=13 Hz, PhCHHS), 3.66 (2H, m, PhCH2CO), 3.11 (1H, dd, J=13, 5 Hz, CHHCHN), 2.99 (1H, dd, J=13, 8 Hz, CHHCHN); ESI-LCMS e/z calcd for C32H27N3O6S 581.646, found 582 (M+H)+, 604 (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-4f12f4d1314d41ae89b3304c88990bfc
Source dataset
uspto-grants-2009_03
Patent number
US07498356B2

Reaction notes

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