Triethylamine → HCID 86757533, compound

HRID 382636Notes

Reaction equation

HRID 382636 reaction equation
[CH2:1]([O:4][C:5]([C:7](=[P:27]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[N:8]1[C@H:11]([CH2:12][C:13]([OH:15])=[O:14])[C@@H:10]([C@H:16]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH3:17])[C:9]1=[O:26])=[O:6])[CH:2]=[CH2:3].C(N(CC)CC)C.[C:53](Cl)(=[O:58])[C:54]([CH3:57])([CH3:56])[CH3:55]>C1(C)C=CC=CC=1>[CH2:1]([O:4][C:5]([C:7](=[P:27]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[N:8]1[C@H:11]([CH2:12][C:13]([O:15][C:53](=[O:58])[C:54]([CH3:57])([CH3:56])[CH3:55])=[O:14])[C@@H:10]([C@H:16]([O:18][Si:19]([C:22]([CH3:24])([CH3:23])[CH3:25])([CH3:21])[CH3:20])[CH3:17])[C:9]1=[O:26])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 86757534HCID 86757534, compound

Product 1

HCID 86757533HCID 86757533, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 0.65 g of (3S,4R)-1-[(allyloxycarbonyl)(triphenylphosphoranylidene)methyl]-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-(carboxymethyl)azetidine-2-one in 4 ml of toluene were added under ice-cooling 0.14 ml of triethylamine and 0.12 ml of pivaloyl chloride, and the mixture was stirred at room temperature. The resulting precipitate was collected by filtration, and the filtrate was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1) to give 0.60 g of (3S,4R)-1-[(allyloxycarbonyl)(triphenylphosphoranylidene)methyl]-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(pivaloyloxycarbonyl)methyl]azetidine-2-one.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customthe filtrate was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-05a4385699c24f4e984d45daa12d6484
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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