Tert-butoxycarbonylalanine → HCID 70980479, compound

HRID 1749113Notes

Reaction equation

FC(F)(F)C(O)=O.[NH2:8][C:9]1[CH:10]=[CH:11][C:12]2[N:17]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[C:16](=[O:25])[C:15]([CH2:28][CH3:29])([CH2:26][CH3:27])[O:14][C:13]=2[N:30]=1.[C:31]([O:35][C:36]([NH:38][C@H:39]([C:41](O)=[O:42])[CH3:40])=[O:37])([CH3:34])([CH3:33])[CH3:32]>>[C:31]([O:35][C:36](=[O:37])[NH:38][C@H:39]([C:41](=[O:42])[NH:8][C:9]1[CH:10]=[CH:11][C:12]2[N:17]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[C:16](=[O:25])[C:15]([CH2:28][CH3:29])([CH2:26][CH3:27])[O:14][C:13]=2[N:30]=1)[CH3:40])([CH3:32])([CH3:33])[CH3:34]

Participants

Reactant 2

HCID 85082Tert-butoxycarbonylalanine

HCID 70979600HCID 70979600, compound

Product 1

HCID 70980479HCID 70980479, compoundYield 66.4%

Procedure

6-Amino-1-(4-chloro-phenyl)-3,3-diethyl-1H-pyrido[2,3-b][1,4]oxazin-2-one trifluoroacetate salt (Example 5, product from Step 3) (235 mg, 0.53 mmol) was coupled with N-(tert-butoxycarbonyl)-L-alanine (255 mg, 1.32 mmol) by following procedures similar to those described in General Procedure 2 to give {(S)-1-[1-(4-chloro-phenyl)-3,3-diethyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-ylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester (177 mg) as a colourless gum. MS: [M+H]+503.

Sources & evidence

ORD record: ord-261d669dc0cb49e2be1f9cd4eb9ee341
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09155743B2

Reaction notes

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