Sodium Hydroxide → HCID 54299414, compound

HRID 280933Notes

Reaction equation

HRID 280933 reaction equation
C([O:3][C:4]([C@@H:6]([NH:15][C@@H:16]1[C:22](=[O:23])[N:21]([CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:20]2[CH:32]=[CH:33][CH:34]=[CH:35][C:19]=2[O:18][CH2:17]1)[CH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:5])C.[OH-].[Na+]>C(O)C.O>[C:4]([C@@H:6]([NH:15][C@@H:16]1[C:22](=[O:23])[N:21]([CH2:24][C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[C:20]2[CH:32]=[CH:33][CH:34]=[CH:35][C:19]=2[O:18][CH2:17]1)[CH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)([OH:5])=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70046884HCID 70046884, compound

Product 1

HCID 54299414HCID 54299414, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In 10 ml of ethanol is dissolved 1.5 g of tert-butyl 3(S)-[1(S)-ethoxycarbonyl-3-cyclohexylpropyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate obtained in Example 49, and 1N sodium hydroxide solution is added dropwise over a period of 15 minutes. After stirring for 3 hours, the solution is diluted with water (200 ml) and extracted with ethyl ether (100 ml). The aqueous layer is acidified slightly with 1N hydrochloric acid to deposit crystals. This product is collected by filtration and dried to give 1.2 g of tert-butyl 3(S)-[1(S)-carboxy-3-cyclohexylpropyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate as colorless needles, melting at 180°-183° C.

Workup

  1. additionis added dropwise over a period of 15 minutes
  2. extractionextracted with ethyl ether (100 ml)
  3. filtrationThis product is collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-1aca764c344b4fada31ec13bb7b02130
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

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