Water → (2R)-Methyl-3-[4'-(2-benzylbenzofuran-3-yl)biphen-4-ylmethylsulfanyl]-2-tert-butoxycarbonylaminopropionate

HRID 900351Notes

Reaction equation

HRID 900351 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C@H:4]([CH2:13][SH:14])[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[CH2:16]([C:23]1[O:24][C:25]2[CH:45]=[CH:44][CH:43]=[CH:42][C:26]=2[C:27]=1[C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][C:37]([CH2:40]Br)=[CH:36][CH:35]=2)=[CH:30][CH:29]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH3:1][O:2][C:3](=[O:15])[C@@H:4]([NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7])[CH2:13][S:14][CH2:40][C:37]1[CH:36]=[CH:35][C:34]([C:31]2[CH:30]=[CH:29][C:28]([C:27]3[C:26]4[CH:42]=[CH:43][CH:44]=[CH:45][C:25]=4[O:24][C:23]=3[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:33][CH:32]=2)=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 10977409N-(tert-Butoxycarbonyl)-L-cysteine methyl esterHCID 596961782-Benzyl-3-(4'-bromomethylbiphen-4-yl)benzofuran

Product 1

HCID 131726824(2R)-Methyl-3-[4'-(2-benzylbenzofuran-3-yl)biphen-4-ylmethylsulfanyl]-2-tert-butoxycarbonylaminopropionateYield 92.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Boc-L-Cysteine methyl ester (260 mg, 0.23 mL, 1.1 mmol) was added dropwise to a stirred suspension of 2-Benzyl-3-(4′-bromomethylbiphen-4-yl)benzofuran (500 mg, 1.1 mmol) and cesium carbonate (720 mg, 2.21 mmol) in anhydrous dimethylformamide (20 mL). The reaction was stirred at room temperature for 2 hrs (TLC control) and then poured into water (100 mL) and extracted with diethyl ether (3×100 mL). The combined extract was washed with water, brine (3×), dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification using 30% ethyl acetate in heptane as eluent afforded the title compound as a white solid (620 mg, 92%): 1H NMR (CDCl3, 300 MHz): δ 7.70 (2H, m, Ar—H), 7.64 (2H, m, Ar—H), 7.60 (3H, m, Ar—H), 7.48 (1H, m, Ar—H), 7.42 (2H, m, Ar—H), 7.26-7.36 (7H, m, Ar—H), 5.32 (1H, d, J=8 Hz, NH), 4.58 (1H, m, CHN), 4.26 (2H, PhCH2), 3.79 (2H, s, PhCH2S), 3.76 (3H, s, OMe), 2.95 (1H, dd, J=13, 5 Hz, CHHCHN), 2.84 (1H, dd, J=13, 7 Hz, CHHCHN), 1.46 (9H, s, CMe3); ESI-LCMS e/z calcd for C37H37NO5S 607.760, found 608 (M+H)+, 630 (M+Na)+.

Workup

  1. extractionextracted with diethyl ether (3×100 mL)
  2. extractionThe combined extract
  3. washwas washed with water, brine (3×)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification

Sources & evidence

ORD record
ord-6da2699f38ac447dba11a959fd4b5b47
Source dataset
uspto-grants-2008_04
Patent number
US07358248B2

Reaction notes

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