(2S, 3S)-3-(5-chloroindole-2-carbonylamino)-2-methyl-2,3-dihydro-1,5-benzoxazepin-4 (5H)-one → (2S, 3R)-3-(5-chloroindole-2-carbonylamino)-2-methyl-2,3-dihydro-1,5-benzoxazepin-4 (5H)-one

HRID 11596Notes

Reaction equation

HRID 11596 reaction equation
FC(F)(F)C(O)=O.N[C@H]1C(=O)NC2C=CC=CC=2O[C@H]1C.[Cl:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][C:27]([C:32]([NH:34][C@@H:35]1[C:41](=[O:42])[NH:40][C:39]3[CH:43]=[CH:44][CH:45]=[CH:46][C:38]=3[O:37][C@H:36]1[CH3:47])=[O:33])=[CH:26]2.FC(F)(F)C(O)=O.N[C@@H]1C(=O)NC2C=CC=CC=2O[C@H]1C>>[Cl:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][C:27]([C:32]([NH:34][C@H:35]1[C:41](=[O:42])[NH:40][C:39]3[CH:43]=[CH:44][CH:45]=[CH:46][C:38]=3[O:37][C@H:36]1[CH3:47])=[O:33])=[CH:26]2

Participants

4

Reactant 3

HCID 10067708(2S, 3S)-3-(5-chloroindole-2-carbonylamino)-2-methyl-2,3-dihydro-1,5-benzoxazepin-4 (5H)-oneHCID 69195761(2S, 3S)-3-amino-2-methyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one trifluoroacetate saltHCID 69196397HCID 69196397, compound

Product 1

HCID 11559723(2S, 3R)-3-(5-chloroindole-2-carbonylamino)-2-methyl-2,3-dihydro-1,5-benzoxazepin-4 (5H)-one

Procedure

The title compound was prepared from (2S,3R)-3-amino-2-methyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one trifluoroacetate salt by the procedures described for the preparation of (2S,3S)-3-(5-chloroindole-2-carbonylamino)-2-methyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one (Example 22) from (2S,3S)-3-amino-2-methyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one trifluoroacetate salt. HPLC/MS [M+H]+, 370.

Sources & evidence

ORD record
ord-659e4f7223dd4a359a81bd1f34cd5b0f
Source dataset
uspto-grants-2006_08
Patent number
US07098235B2

Reaction notes

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