Lithium hydroxide, monohydrate → N-[(S)-alpha-[[[1-methyl-1-[methyl-[2-(2-pyridyl)ethyl]carbamoyl]ethyl]sulfonyl]methyl]hydrocinnamoyl]-3-(thiazol-4-yl)-D,L-alanine

HRID 275626Notes

Reaction equation

HRID 275626 reaction equation
C[O:2][C:3](=[O:41])[CH:4]([CH2:35][C:36]1[N:37]=[CH:38][S:39][CH:40]=1)[NH:5][C:6](=[O:34])[C@@H:7]([CH2:15][S:16]([C:19]([CH3:33])([C:21](=[O:32])[N:22]([CH3:31])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1)[CH3:20])(=[O:18])=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.[OH-].[Li+]>O1CCOCC1.O>[CH3:33][C:19]([S:16]([CH2:15][C@@H:7]([CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:6]([NH:5][CH:4]([C:3]([OH:41])=[O:2])[CH2:35][C:36]1[N:37]=[CH:38][S:39][CH:40]=1)=[O:34])(=[O:18])=[O:17])([C:21](=[O:32])[N:22]([CH3:31])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1)[CH3:20]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 54195495N-[(S)-alpha-[[[1-methyl-1-[methyl-[2-(2-pyridyl)ethyl]carbamoyl]ethyl]sulfonyl]methyl]hydrocinnamoyl]-3-(thiazol-4-yl)-D,L-alanine methyl ester

Product 1

HCID 18659451N-[(S)-alpha-[[[1-methyl-1-[methyl-[2-(2-pyridyl)ethyl]carbamoyl]ethyl]sulfonyl]methyl]hydrocinnamoyl]-3-(thiazol-4-yl)-D,L-alanineYield 124.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 300 mg of N-[(S)-α-[[[1-methyl-1-[methyl-[2-(2-pyridyl)ethyl]carbamoyl]ethyl]sulfonyl]methyl]hydrocinnamoyl]-3-(thiazol-4-yl)-D,L-alanine methyl ester in 2.5 ml of dioxan was treated with a solution of 24.3 mg of lithium hydroxide hydrate in 1 ml of water and stirred at 50 for 3 hours. Subsequently, the solution was partitioned between ethyl acetate and water and the organic phase was extracted three times with water. The aqueous extracts were adjusted to pH 2 with ethyl acetate and with 2N hydrochloric acid and evaporated under reduced pressure. There were obtained 365 mg of N-[(S)-α-[[[1 -methyl-1-[methyl-[2-(2-pyridyl)ethyl]carbamoyl]ethyl]sulfonyl]methyl]hydrocinnamoyl]-3-(thiazol-4-yl)-D ,L-alanine as a colourless foam which was used directly in the next step.

Workup

  1. customSubsequently, the solution was partitioned between ethyl acetate and water
  2. extractionthe organic phase was extracted three times with water
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e57d4348d3e94caba79d3cc533542fc7
Source dataset
uspto-grants-1995_02
Patent number
US05393875

Reaction notes

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