(2R,3S)-3-amino-2-methyl-2,3-dihydrobenzo[b][1,4]-oxazepin-4 (5H)-one → Methyl-[(S)-1-((6R,7S)-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclo hepten-7-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

HRID 1055365Notes

Reaction equation

HRID 1055365 reaction equation
[CH3:1][N:2]([C@@H:10]([CH3:26])[C:11](=[O:25])[NH:12][C@H:13]1[CH2:19][O:18][C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[NH:15][C:14]1=[O:24])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].N[C@H:28]1[C@@H](C)OC2C=CC=CC=2NC1=O>>[C:5]([O:4][C:3](=[O:9])[N:2]([CH3:1])[C@H:10]([C:11](=[O:25])[NH:12][C@@H:13]1[C:14](=[O:24])[NH:15][C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=2[O:18][C@@H:19]1[CH3:28])[CH3:26])([CH3:8])([CH3:6])[CH3:7]

Participants

3

Reactant 2

HCID 67076981(2R,3S)-3-amino-2-methyl-2,3-dihydrobenzo[b][1,4]-oxazepin-4 (5H)-oneHCID 72713380tert-Butyl methyl((S)-1-oxo-1-((S)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)propan-2-yl)carbamate

Product 1

HCID 90060608Methyl-[(S)-1-((6R,7S)-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclo hepten-7-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl esterYield 61%

Procedure

In a similar manner to that described for the preparation of tert-butyl methyl((S)-1-oxo-1-((S)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)propan-2-yl)carbamate except the mixture was stirred 1.5 h and the crude product purified by silica gel chromatography, (2R,3S)-3-amino-2-methyl-2,3-dihydrobenzo[b][1,4]-oxazepin-4 (5H)-one (420 mg, 2.19 mmol) was converted to the title compound (505 mg, 61%) as a white foam.

Sources & evidence

ORD record
ord-2bf1d84381f7419ba04454ebb6459d84
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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