[(3S,6R)-6-(6-azido-hexyloxy)-1-methyl-2-oxo-azepan-3-yl]-carbamic acid tert-butyl ester → (3S,6S)-3-amino-6-azido-azepan-2-one

HRID 2224032Notes

Reaction equation

HRID 2224032 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:14][CH2:13][C@H:12]([N:15]=[N+:16]=[N-:17])[CH2:11][NH:10][C:9]1=[O:18])(C)(C)C.C(OC(=O)N[C@H]1CC[C@@H](OCCCCCCN=[N+]=[N-])CN(C)C1=O)(C)(C)C>>[NH2:7][C@H:8]1[CH2:14][CH2:13][C@H:12]([N:15]=[N+:16]=[N-:17])[CH2:11][NH:10][C:9]1=[O:18]

Participants

3

Reactant 2

HCID 86609579[(3S,6R)-6-(6-azido-hexyloxy)-1-methyl-2-oxo-azepan-3-yl]-carbamic acid tert-butyl esterHCID 86609581((3S,6S)-6-azido-2-oxo-azepan-3-yl)-carbamic acid tert-butyl ester

Product 1

HCID 86609582(3S,6S)-3-amino-6-azido-azepan-2-one

Procedure

Following the procedure of example 2d) ((3S,6S)-6-azido-2-oxo-azepan-3-yl)-carbamic acid tert-butyl ester is substituted for [(3S,6R)-6-(6-azido-hexyloxy)-1-methyl-2-oxo-azepan-3-yl]-carbamic acid tert-butyl ester to give (3S,6S)-3-amino-6-azido-azepan-2-one. MS (ESI) 170 (M+H)+

Sources & evidence

ORD record
ord-104510962f5d4b629f12561a374cd650
Source dataset
uspto-grants-2008_05
Patent number
US07378410B2

Reaction notes

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