HCID 11387776, compound → HCID 11411038, compound

HRID 1782651Notes

Reaction equation

HRID 1782651 reaction equation
B1([O-])OO1.[OH2:5].[OH2:6].O.O.[Na+].[CH2:10]([C:17]1[O:18][C:19]2[CH:52]=[CH:51][CH:50]=[CH:49][C:20]=2[C:21]=1[C:22]1[CH:48]=[CH:47][C:25]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32][S:33][CH2:34][C@H:35]([NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C:36]([OH:38])=[O:37])=[CH:28][CH:27]=2)=[CH:24][CH:23]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)(=O)C.C(OCC)(=O)C>[CH2:10]([C:17]1[O:18][C:19]2[CH:52]=[CH:51][CH:50]=[CH:49][C:20]=2[C:21]=1[C:22]1[CH:23]=[CH:24][C:25]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32][S:33]([CH2:34][C@H:35]([NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:44])[CH3:45])=[O:41])[C:36]([OH:38])=[O:37])(=[O:6])=[O:5])=[CH:28][CH:27]=2)=[CH:47][CH:48]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 11387776HCID 11387776, compoundHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

Product 1

HCID 11411038HCID 11411038, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

Sodium perborate tetrahydrate (320 mg, 2.1 mmol) was added as a solid to a stirred solution of (2R)-3-[4′-(2-benzylbenzofuran-3-yl)biphen-4-ylmethylsulfanyl]-2-tert-butoxycarbonylamino-propionic acid (440 mg, 0.74 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 of the product by flash column chromatography, using 15% methanol in methylene chloride as eluent, afforded the title compound as a white solid (426 mg, 92%): mp. 202-203° C. Rf 0.40 (20% methanol in dichloromethane). 1H NMR (DMSO-d6, 300 MHz) δ 7.84 (2H, d, J=9 Hz, Ar—H), 7.74 (2H, d, J=9 Hz, Ar—H), 7.60 (4H, m, Ar—H), 7.48 (2H, d, J=9 Hz, Ar—H), 7.29 (5H, m, Ar—H), 7.22 (2H, d, J=8 Hz, Ar—H), 6.58 (1H, br s, NH), 4.51 (2H, s, PhCH2), 4.27 (2H, s, PhCH2S), 4.16 (1H, m, CHN), 3.56 (1H, dd, J=15, 5 Hz, CHHCHN), 3.20 (1H, dd, J=15, 8 Hz, CHHCHN), 1.37 (9H, s, tBu); ESI-LCMS e/z calcd for C36H35NO7S 625.739, found 626 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-baf9dffcf2204eb8856112afb74bef5b
Source dataset
uspto-grants-2009_03
Patent number
US07498356B2

Reaction notes

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