1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl (2S,3S)-2,8-dimethyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamate

HRID 1055375Notes

Reaction equation

HRID 1055375 reaction equation
CC1C=CC2NC(=O)[C@@H](NC(=O)OC(C)(C)C)COC=2C=1.CCN=C=NCCCN(C)C.[NH2:33][C:34]1[CH:54]=[CH:53][C:52]([CH3:55])=[CH:51][C:35]=1[O:36][C@@H:37]([CH3:50])[C@H:38]([NH:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C:39](O)=[O:40]>>[CH3:50][C@@H:37]1[O:36][C:35]2[CH:51]=[C:52]([CH3:55])[CH:53]=[CH:54][C:34]=2[NH:33][C:39](=[O:40])[C@H:38]1[NH:42][C:43](=[O:44])[O:45][C:46]([CH3:49])([CH3:48])[CH3:47]

Participants

4

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 67076736(S)-tert-butyl 8-methyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamateHCID 90037055(2S,3S)-3-(2-amino-5-methyl-phenoxy)-2-tert-butoxycarbonylamino-butyric acid

Product 1

HCID 131736347tert-butyl (2S,3S)-2,8-dimethyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamateYield 55.5%

Procedure

In a similar manner to that described for the preparation of (S)-tert-butyl 8-methyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamate, except 1.5 eq. of EDCI was used, (2S,3S)-3-(2-amino-5-methyl-phenoxy)-2-tert-butoxycarbonylamino-butyric acid (290 mg, 894 μmol) was converted to tert-butyl (2S,3S)-2,8-dimethyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamate (152 mg, 55.5% yield) as a solid.

Sources & evidence

ORD record
ord-82a0666f9c1146ba8fa44279c4357eae
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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