Ethanol → HCID 131715488, compound

HRID 648831Notes

Reaction equation

HRID 648831 reaction equation
[C:1]([NH:9][CH:10]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:11](=[O:36])[CH2:12][N:13]([C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])[C@H:14]([C:16]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([OH:22])=[O:21])=[O:17])[CH3:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:44](O)[CH3:45].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.O1CCCC1>[C:1]([NH:9][CH:10]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:11](=[O:36])[CH2:12][N:13]([C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])[C@H:14]([C:16]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20]([O:22][CH2:44][CH3:45])=[O:21])=[O:17])[CH3:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 10868DicyclohexylcarbodiimideHCID 14127420HCID 14127420, compound

Product 1

HCID 131715488HCID 131715488, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(±)-1-[N-[3-(Benzoylamino)-2-oxo-4-phenylbutyl]-N-[(phenylmethoxy)carbonyl]-L-alanyl]-L-proline (1.17 g., 2 mmole), prepared as set forth in Example 109 (d), is taken into tetrahydrofuran (2 ml.) with stirring in an ice-bath. To this is added absolute ethanol (2.3 ml., 40 mmole) followed by 4-dimethylamino pyridine (122 mg., 1 mmole) and dicyclohexylcarbodiimide (412 mg., 2 mmole). The reaction is allowed to run overnight at room temperature. The dicyclohexylurea is filtered off, the filtrate is concentrated to dryness, the residue is taken into ethyl acetate and washed neutral with 10% potassium bisulfate and saturated sodium carbonate. The crude product (1.2 g.) is purified on silica gel column in benzene: acetic acid (8:2) to yield 1.0 g. of (±)-1-[N-[3-(benzoylamino)-2-oxo-4-phenylbutyl]-N-[(phenylmethoxy)carbonyl]-L-proline, ethyl ester.

Workup

  1. filtrationThe dicyclohexylurea is filtered off
  2. concentrationthe filtrate is concentrated to dryness
  3. washwashed neutral with 10% potassium bisulfate and saturated sodium carbonate
  4. customThe crude product (1.2 g.) is purified on silica gel column in benzene: acetic acid (8:2)
  5. customto yield 1.0 g

Sources & evidence

ORD record
ord-484e942d69cb4bce913c71d20205405b
Source dataset
uspto-grants-1988_04
Patent number
US04736066

Reaction notes

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