Cyclohexane → t-Butyl rel-alpha-[3(S)-(8-t-butoxycarbonylamino-1-ethoxycarbonyloctylamino)-2-oxo-6(R)-phenylperhydroazepin-1-yl]acetate

HRID 868244Notes

Reaction equation

HRID 868244 reaction equation
[NH2:1][C@H:2]1[CH2:8][CH2:7][C@H:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][N:4]([CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:3]1=[O:23].Br[CH:25]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C:26]([O:28][CH2:29][CH3:30])=[O:27].C1CCCCC1>C(OCC)(=O)C>[C:42]([O:41][C:39]([NH:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH:25]([NH:1][C@H:2]1[CH2:8][CH2:7][C@H:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][N:4]([CH2:15][C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[C:3]1=[O:23])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:40])([CH3:45])([CH3:44])[CH3:43]

Participants

5

Reactant 3

HCID 8078CyclohexaneHCID 14003452t-butyl rel-alpha-[3(S)-amino-2-oxo-6(R)-phenylperhydroazepin-1-yl]acetateHCID 21287862HCID 21287862, compound

Product 1

HCID 22840211t-Butyl rel-alpha-[3(S)-(8-t-butoxycarbonylamino-1-ethoxycarbonyloctylamino)-2-oxo-6(R)-phenylperhydroazepin-1-yl]acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.2 g of t-butyl rel-α-[3(S)-amino-2-oxo-6(R)-phenylperhydroazepin-1-yl]acetate was treated with 2.15 g of ethyl 2-bromo-9-t-butoxycarbonylaminononanoate prepared as described in Preparation 4) in a similar manner to that described in Example 4, to afford a reaction product, which was subjected to column chromatography through silica gel using a mixture of cyclohexane and ethyl acetate in the ratio of 1:1 by volume as the eluent.

Workup

  1. customprepared
  2. customas described in Preparation 4) in a similar manner to that
  3. customto afford a reaction product, which

Sources & evidence

ORD record
ord-325d7bd5fabc4ea5a8f6387f5204d9ab
Source dataset
uspto-grants-1988_10
Patent number
US04778790

Reaction notes

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