1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (S)-3-Amino-8-trifluormethyl-2,3-dihydrobenzo[b][1,4]oxazepin-4 (5H)-one trifluoroacetate

HRID 1055379Notes

Reaction equation

HRID 1055379 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]C2C=C(C)C=CC=2N[C:10]1=[O:21].CCN=C=NCCCN(C)C.C(OC(N[C@@H](CO)C(O)=O)=O)(C)(C)C.F[C:48]1[CH:53]=[C:52]([C:54]([F:57])([F:56])[F:55])[CH:51]=[CH:50][C:49]=1[N+:58]([O-])=O>CCOCC.CCCCC>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][C@H:9]1[CH2:10][O:21][C:48]2[CH:53]=[C:52]([C:54]([F:57])([F:56])[F:55])[CH:51]=[CH:50][C:49]=2[NH:58][C:15]1=[O:14]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 37221693-fluoro-4-nitrobenzotrifluorideHCID 90037368HCID 90037368, compound

Product 1

HCID 118574046(S)-3-Amino-8-trifluormethyl-2,3-dihydrobenzo[b][1,4]oxazepin-4 (5H)-one trifluoroacetate

Reagents, catalysts & solvents 1

HCID 21877078Diethylether pentaneSolvent

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 1.2 eq. EDCI was used and the reaction mixture was stirred for 2 h and in Step 4 the mixture was stirred for 1 h and the material obtained was tritrurated with Et2O/pentane, (S)-2-(tert-butoxycarbonylamino)-3-hydroxypropanoic acid (4.96 g, 24.2 mmol) and 2-fluoro-1-nitro-4-(trifluoromethyl)benzene (5.05 g, 24.2 mmol) were converted to the title compound (1.6 g) as a pale yellow solid.

Workup

  1. stirringwas stirred for 1 h
  2. customthe material obtained

Sources & evidence

ORD record
ord-5c211a8cbfa2402fa3ad277c789c1ca9
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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