Ethanol → HCID 88617846, compound

HRID 231940Notes

Reaction equation

HRID 231940 reaction equation
[OH:1][P:2]([CH:24]([NH:32][C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([O:4][C@@H:5]([CH3:23])[C:6]([N:8]1[CH2:22][CH2:21][CH2:20][C@H:9]1[C:10]([O:12]CC1C=CC=CC=1)=[O:11])=[O:7])=[O:3].C(O)C>O1CCOCC1.[OH-].[Li+].O>[OH:3][P:2]([CH:24]([NH:32][C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)([O:4][C@@H:5]([CH3:23])[C:6]([N:8]1[CH2:22][CH2:21][CH2:20][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7])=[O:1]

Participants

6

Reactant 2

HCID 702EthanolHCID 131716002HCID 131716002, compound

Product 1

HCID 88617846HCID 88617846, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3939Lithium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

The phenylmethyl ester product from part (a) (4.12 g., 6.9 mmole) is dissolved in dioxane (15 ml.) and 1N lithium hydroxide (15 ml.). Ethanol (several ml.) is added to solubilize the salts, and the reaction mixture is stirred overnight at room temperature under argon. The reaction mixture is diluted with water and washed with ether and ethyl acetate. This aqueous solution is acidified and extracted with ethyl acetate. This ethyl acetate solution is washed with brine, dried over sodium sulfate, and concentrated to give 1-[(S)-2-[[hydroxy[2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinyl]oxy]-1-oxopropyl]-L-proline as a viscous white oil.

Workup

  1. washwashed with ether and ethyl acetate
  2. extractionextracted with ethyl acetate
  3. washThis ethyl acetate solution is washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-89df3e66d71d482d8d93e9e30f9935f9
Source dataset
uspto-grants-1989_07
Patent number
US04849414

Reaction notes

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