Ethanol → HCID 86583528, compound

HRID 1066582Notes

Reaction equation

HRID 1066582 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:13]([CH:15]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=2)[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P([O-])(OCC)(SCC)=[S:38].C(O)C>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:13]([CH:15]([NH:21][C:22]2[CH:23]=[CH:24][C:25]([C:28](=[S:38])[NH2:29])=[CH:26][CH:27]=2)[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 53249491DiethyldithiophosphateHCID 86583529HCID 86583529, compound

Product 1

HCID 86583528HCID 86583528, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.7 g of ethyl (RS)-(5-benzyloxy-2-ethoxycarbonylmethoxy-phenyl)-(4-cyano-phenylamino)-acetate, 1.13 ml of diethyl dithiophosphate and 4 ml of ethanol were heated for 2 hrs. to 60° C. The reaction mixture was diluted with ethyl acetate, washed with saturated sodium hydrogen carbonate solution, water and saturated sodium chloride solution, dried and evaporated in a vacuum. Chromatography on silica gel gave 1.6 g of ethyl (RS)-(5-benzyloxy-2-ethoxycarbonylmethoxy-phenyl)-(4-thiocarbamoyl-phenylamino)-acetate, m.p. 166° C., MS: 523 (M+H)+.

Workup

  1. customto 60° C
  2. washwashed with saturated sodium hydrogen carbonate solution, water and saturated sodium chloride solution
  3. customdried
  4. customevaporated in a vacuum

Sources & evidence

ORD record
ord-dcc6daa7b5594d09abcb569e964efbe0
Source dataset
uspto-grants-2001_06
Patent number
US06242644B1

Reaction notes

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