Picolyl chloride → HCID 10690937, compound

HRID 2224033Notes

Reaction equation

[C:1]([O:5][C:6](=[O:16])[NH:7][C@H:8]1[CH2:14][CH2:13][CH2:12][CH2:11][NH:10][C:9]1=[O:15])([CH3:4])([CH3:3])[CH3:2].C(OC(=O)N[C@H]1CC[C@@H](O[Si](C(C)(C)C)(C)C)CNC1=O)(C)(C)C.[CH2:41]([O:48][C:49](=[O:52])[CH2:50]Br)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.ClCC1C=CC=CN=1>>[CH2:41]([O:48][C:49](=[O:52])[CH2:50][N:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C@H:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:16])[C:9]1=[O:15])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

Reactant 4

HCID 23393Picolyl chloride

HCID 62576Benzyl bromoacetate

HCID 7022178(S)-tert-Butyl (2-oxoazepan-3-yl)carbamate

HCID 11728063[(3S,6R)-6-(tert-butyl-dimethyl-silanyloxy)-2-oxo-azepan-3-yl]-carbamic acid tert-butyl ester

Product 1

HCID 10690937HCID 10690937, compound

Procedure

Following the procedure of example 1h) except ((S)-2-oxo-azepan-3-yl)-carbamic acid tert-butyl ester is substituted for [(3S,6R)-6-(tert-butyl-dimethyl-silanyloxy)-2-oxo-azepan-3-yl]-carbamic acid tert-butyl ester and bromo-acetic acid benzyl ester is substituted for 2-chloromethyl-pyridine and one equivalent of KN(Si(CH3)3)2 base to give ((S)-3-tert-butoxycarbonylamino-2-oxo-azepan-1-yl)-acetic acid benzyl ester. Removal of the Boc group by procedure 2d) gives ((S)-3-amino-2-oxo-azepan-1-yl)-acetic acid benzyl ester.

Sources & evidence

ORD record: ord-141c823260794ddb8e44681b3a4b3744
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378410B2

Reaction notes

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