Tetrahydrofuran → HCID 53642168, compound

HRID 1679210Notes

Reaction equation

HRID 1679210 reaction equation
[CH:1]1([CH2:4][O:5][C:6]([S:8][CH:9]2[N:12]([C:13](=[C:27]([OH:29])[CH3:28])[C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)=[O:15])[C:11](=[O:30])[CH:10]2[NH:31][C:32](=[O:41])[CH2:33][O:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:7])[CH2:3][CH2:2]1.O1CCCC1.CN(P(N(C)C)(N(C)C)=O)C.[CH3:58][S:59](Cl)(=[O:61])=[O:60]>C(N(CC)CC)C>[CH:1]1([CH2:4][O:5][C:6]([S:8][CH:9]2[N:12]([C:13](=[C:27]([O:29][S:59]([CH3:58])(=[O:61])=[O:60])[CH3:28])[C:14]([O:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=3)=[O:15])[C:11](=[O:30])[CH:10]2[NH:31][C:32](=[O:41])[CH2:33][O:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:7])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 12679HexamethylphosphoramideHCID 31297Methanesulfonyl chlorideHCID 86735544HCID 86735544, compound

Product 1

HCID 53642168HCID 53642168, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of p-nitrobenzyl α-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidin-1-yl]-α-(1-hydroxyethylidene)acetate (904 mg) in a mixture (9.5 ml) of tetrahydrofuran and hexamethylphosphorotriamide (20:1) are added methanesulfonyl chloride (0.26 ml) and triethylamine (0.37 ml). After 2 hours, the reaction mixture is poured into ice water, and extracted with chloroform. The extract solution is washed with water, dried, and evaporated to give p-nitrobenzyl α-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidin-1-yl]-α-(1-methanesulfonyloxyethylidene)acetate (1.12 g). Yellow foam. IR: νmaxCHCl3 3426, 1785, 1722-1704br, 1640, 1601, 1160, 1175, 986 cm-1. NMR: δCDCl3 0.32-1.25m5H, 2.57s3H, 2.72s3H, 3.99d(7Hz)2H, 4.55s2H, 5.33-5.99m4H, 6.82-7.62m7H, 8.21d(8.5Hz).2H

Workup

  1. extractionextracted with chloroform
  2. washThe extract solution is washed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-db06c42cd6ed4425a74c65e2f2ec0cc9
Source dataset
uspto-grants-1978_03
Patent number
US04079181

Reaction notes

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