Hydrogen chloride-ethyl acetate → 3(S)-[1(R)-ethoxycarbonyl-3-cyclohexylpropyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetic acid hydrochloride

HRID 280928Notes

Reaction equation

HRID 280928 reaction equation
[CH2:1]([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]CC2C=CC=CC=2)=[O:26])[C:20]2[CH:35]=[CH:36][CH:37]=[CH:38][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])[CH3:2].C(OCC)(=O)C.[ClH:45]>[C].[Pd].CCOCC>[ClH:45].[CH2:1]([O:3][C:4]([C@H:6]([NH:15][C@@H:16]1[C:22](=[O:23])[N:21]([CH2:24][C:25]([OH:27])=[O:26])[C:20]2[CH:35]=[CH:36][CH:37]=[CH:38][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])[CH3:2]

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 70046892benzyl 3(S)-[1(R)-ethoxycarbonyl-3-cyclohexylpropyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate

Product 1

HCID 700498693(S)-[1(R)-ethoxycarbonyl-3-cyclohexylpropyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetic acid hydrochloride

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

Catalytic reduction of benzyl 3(S)-[1(R)-ethoxycarbonyl-3-cyclohexylpropyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate (0.35 g) obtained in Example 21 is carried out using 10% palladium-carbon as a catalyst in a manner similar to that described in Example 17. The oily product is dissolved in ether, and 0.5 ml of hydrogen chloride-ethyl acetate solution (5N) is added dropwise to the solution to give 0.18 g of 3(S)-[1(R)-ethoxycarbonyl-3-cyclohexylpropyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetic acid hydrochloride as a colorless powder.

Sources & evidence

ORD record
ord-93a97671a06242fbb92bd3042840d4ee
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

Loading…