(S)-tert-Butyl (4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)carbamate → (S)-Methyl 3-(tert-butoxycarbonylamino)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine-9-carboxylate

HRID 1055362Notes

Reaction equation

HRID 1055362 reaction equation
O=C1[C@@H](NC(=O)OC(C)(C)C)COC2C=CC=CC=2N1.[NH2:21][C:22]1[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([O:44][CH3:45])=[O:43])[C:23]=1[O:24][CH2:25][C@H:26]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:27](O)=[O:28]>>[C:34]([O:33][C:31]([NH:30][C@H:26]1[CH2:25][O:24][C:23]2[C:38]([C:42]([O:44][CH3:45])=[O:43])=[CH:39][CH:40]=[CH:41][C:22]=2[NH:21][C:27]1=[O:28])=[O:32])([CH3:37])([CH3:36])[CH3:35]

Participants

3

Reactant 2

HCID 18599719(S)-tert-Butyl (4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)carbamateHCID 90036891(S)-3-(2-amino-6-(methoxycarbonyl)phenoxy)-2-(tert-butoxycarbonylamino)propanoic acid

Product 1

HCID 90037664(S)-Methyl 3-(tert-butoxycarbonylamino)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine-9-carboxylateYield 65.8%

Procedure

In a similar manner to that described for the preparation of (S)-tert-butyl 4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamate except the crude product was purified by silica gel chromatography, (S)-3-(2-amino-6-(methoxycarbonyl)phenoxy)-2-(tert-butoxycarbonylamino)propanoic acid (3.9 g, 6.6 mmol) was converted to the title compound (1.46 g, 65%) as a white foam.

Sources & evidence

ORD record
ord-8d14451a1e11416ba55ca2fd6d202dd1
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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