Water → HCID 69116789, compound

HRID 2252432Notes

Reaction equation

HRID 2252432 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([OH:46])[CH:41]=2)[CH:8]=[CH:9][C:10]=1[C@@H:11]1[C@@H:14]([CH2:15][CH2:16][C@H:17]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[C:13](=[O:33])[N:12]1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=O)C.O.C(N(CC)CC)C.C1(C)C=CC=CC=1>CO>[Si:26]([O:25][C@H:17]([C:18]1[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=1)[CH2:16][CH2:15][C@@H:14]1[C@@H:11]([C:10]2[CH:9]=[CH:8][C:7]([C:40]3[CH:45]=[CH:44][CH:43]=[C:42]([OH:46])[CH:41]=3)=[CH:6][C:5]=2[OH:4])[N:12]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:13]1=[O:33])([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 8471TriethylamineHCID 69256517HCID 69256517, compound

Product 1

HCID 69116789HCID 69116789, compoundYield 104.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

4-{(2S,3R)-3-[(3S)-3-{[tert-Butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-oxo-1-phenylazetidin-2-yl}-3′-hydroxybiphenyl-3-yl acetate (70 mg, 0.11 mmol) was dissolved in methanol (2.45 mL). Water (0.73 mL) was added dropwise followed by triethylamine (2.2 mL) and the reaction stirred at room temperature for 1 h. Toluene (3 mL) and methanol (5 mL) were added and the reaction was concentrated to give 69 mg of crude (3R,4S)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-(3,3′-dihydroxybiphenyl-4-yl)-1-phenylazetidin-2-one which was used without further purification.

Workup

  1. concentrationthe reaction was concentrated

Sources & evidence

ORD record
ord-7ba2469d8b784a689f8d0caa19ba6487
Source dataset
uspto-grants-2008_01
Patent number
US07320972B2

Reaction notes

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