4-Fluoro-3-nitrobenzotrifluoride → (S)-3-Amino-7-trifluormethyl-2,3-dihydrobenzo[b][1,4]oxazepin-4 (5H)-one trifluoro acetate

HRID 1055377Notes

Reaction equation

HRID 1055377 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][C@H:9]1[CH2:15][O:14][C:13]2[CH:16]=[C:17](C)[CH:18]=[CH:19][C:12]=2[NH:11][C:10]1=[O:21].C(OC(N[C@@H](CO)C(O)=O)=O)(C)(C)C.FC1C=CC([C:43]([F:46])([F:45])[F:44])=CC=1[N+]([O-])=O>CCCCCC>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][C@H:9]1[CH2:15][O:14][C:13]2[CH:16]=[CH:17][C:18]([C:43]([F:46])([F:45])[F:44])=[CH:19][C:12]=2[NH:11][C:10]1=[O:21]

Participants

5

Reactant 3

HCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 90037368HCID 90037368, compound

Product 1

HCID 90037388(S)-3-Amino-7-trifluormethyl-2,3-dihydrobenzo[b][1,4]oxazepin-4 (5H)-one trifluoro acetate

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

In a similar manner to that described for the preparation of (S)-3-amino-8-methyl-2,3-dihydrobenzo[b][1,4]oxazepin-4(5H)-one trifluoroacetate except in Step 3 the reaction mixture was stirred for 4 h and in the material obtained in Step 4 was triturated with hexane, (S)-2-(tert-butoxycarbonylamino)-3-hydroxypropanoic acid (4.1 g, 20.0 mmol) and 1-fluoro-2-nitro-4-(trifluoromethyl)benzene (4.18 g, 20.0 mmol) were converted to the title compound (1.06 g) which was used without purification.

Sources & evidence

ORD record
ord-641a2c2a454c471092f8e456bab36f0c
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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