Water → HCID 67790986, compound

HRID 1650301Notes

Reaction equation

HRID 1650301 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][C:13](=[O:17])[N:14]([CH3:16])[CH3:15])[CH2:9][C@H:8]1[CH:18]=[C:19]([CH3:38])[C:20](=[O:37])[CH2:21][C@H:22]1[NH:25][C:24](=[O:26])[C@@H:23]1[C@H:27]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH3:28])=[O:6])[CH:2]=[CH2:3].C(N([CH2:44][CH3:45])CC)C.[OH2:46].[C:47]([O:50][CH2:51]C)(=[O:49])[CH3:48]>ClCCl>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][C:13](=[O:17])[N:14]([CH3:15])[CH3:16])[CH2:9][C@H:8]1[CH:18]=[C:19]([CH3:38])[C:20](=[O:37])[CH2:21][C@H:22]1[N:25]([C:48](=[O:46])[C:47]([O:50][CH2:51][CH:44]=[CH2:45])=[O:49])[C:24](=[O:26])[C@@H:23]1[C@H:27]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH3:28])=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 67792060HCID 67792060, compound

Product 1

HCID 67790986HCID 67790986, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of (3S,4R)-4-[4-{(2S,4R)-1-allyloxycarbonyl-4-(dimethylcarbamoyloxy)pyrrolidin-2-yl)-3-methyl-2-oxo-3-butenyl]-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidine (0.33 g) and triethylamine (0.17 ml ) in dichloromethane (10 ml) was added allyl oxalyl chloride (0.13 g) at -20° C. and the resulting mixture was stirred for 30 minutes at -20° C. The reaction mixture was taken up into a mixture of water (50 ml) and ethyl acetate (50 ml). The organic layer was separated, washed in turn with water, aqueous sodium hydrogen carbonate and brine, and dried over magnesium sulfate. Evaporation of the solvent gave allyl 2-[(3S,4R)-4-[4-{(2S,4R)-1-allyloxycarbonyl-4-(dimethylcarbamoyloxy)pyrrolidin-2-yl}-3-methyl-2-oxo-3-butenyl]- 3-{(1R)-1-t-butyldimethylsilyloxyethyl)-2-oxoazetidin-1-yl]glyoxylate (0.26 g).

Workup

  1. customThe organic layer was separated
  2. washwashed in turn with water, aqueous sodium hydrogen carbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-b11c1528f59949d597ae9adc6658f376
Source dataset
uspto-grants-1990_05
Patent number
US04923857

Reaction notes

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