HCID 10615174, compound → HCID 86751789, compound

HRID 1285470Notes

Reaction equation

HRID 1285470 reaction equation
CC(C)(OC([NH:7][C@H:8]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:9]1=[O:21])=O)C.[ClH:23].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:23].[NH2:7][C@H:8]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:9]1=[O:21]

Participants

4

Reactant 2

HCID 10615174HCID 10615174, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 86751789HCID 86751789, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-hexahydro-1H-azepine-1-acetic acid, ethyl ester (1.6 g., 5.0 mmole) and ethyl acetate (5 ml.) at 0° (ice bath) is treated with cold saturated hydrochloric acid/ethyl acetate (40 ml.). After stirring for 45 minutes at 0°, nitrogen is passed through the solution to remove excess hydrochloric acid. The ethyl acetate is evaporated and the resulting oil is triturated with ether (3 times) to give 1.1 g. of (S)-3-amino-2-oxo-hexahydro-1H-azepine-1-acetic acid, ethyl ester, monohydrochloride as a very hygroscopic white crystalline solid after drying in vacuo over phosphorus pentoxide. TLC (methylene chloride/acetic acid/methanol; 8:1:1) major spot at Rf =0.32.

Workup

  1. customto remove excess hydrochloric acid
  2. customThe ethyl acetate is evaporated
  3. customthe resulting oil is triturated with ether (3 times)
  4. customto give 1.1 g
  5. dry with materialof (S)-3-amino-2-oxo-hexahydro-1H-azepine-1-acetic acid, ethyl ester, monohydrochloride as a very hygroscopic white crystalline solid after drying in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-5dffaf9f0dbc4e52bf92ee50dee5ef66
Source dataset
uspto-grants-1986_01
Patent number
US04567167

Reaction notes

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