1,1'-(Diazomethylene)bis(benzene) → (S)-7-[[Ethoxy(4-phenylbutyl)phosphinyl]acetyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, diphenylmethyl ester

HRID 1156812Notes

Reaction equation

HRID 1156812 reaction equation
[CH2:1]([O:3][P:4]([CH2:16][C:17]([N:19]1[C@H:27]([C:28]([OH:30])=[O:29])[CH2:26][C:21]2([S:25][CH2:24][CH2:23][S:22]2)[CH2:20]1)=[O:18])([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:5])[CH3:2].[C:31]1([C:37]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[N+]=[N-])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(OCC)(=O)C>[CH2:1]([O:3][P:4]([CH2:16][C:17]([N:19]1[C@H:27]([C:28]([O:30][CH:37]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[O:29])[CH2:26][C:21]2([S:22][CH2:23][CH2:24][S:25]2)[CH2:20]1)=[O:18])([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 54496794(S)-7-[[Ethoxy(4-phenylbutyl)phosphinyl]acetyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid

Product 1

HCID 86738447(S)-7-[[Ethoxy(4-phenylbutyl)phosphinyl]acetyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, diphenylmethyl esterYield 140.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

(S)-7-[[Ethoxy(4-phenylbutyl)phosphinyl]acetyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid (3.2 g) in ethyl acetate is treated with 2.0 g of diphenyldiazomethane in ethyl acetate. After 3.5 hours, the reaction mixture is partitioned between ethyl acetate and water. The layers are separated and the organic portion is washed with saturated sodium bicarbonate, 5% potassium bisulfate, brine and dried (MgSO4). The solvent is stripped leaving 6.1 g of residue which is chromatographed on 180 g of silica, eluting with ethyl acetate to yield 3.4 g of the title compound as an oil.

Workup

  1. customthe reaction mixture is partitioned between ethyl acetate and water
  2. customThe layers are separated
  3. washthe organic portion is washed with saturated sodium bicarbonate, 5% potassium bisulfate, brine
  4. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-3c234100b80d4830b6073de7a4153d96
Source dataset
uspto-grants-1982_06
Patent number
US04337201

Reaction notes

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