Dichloromethane → HCID 58935426, compound
Reaction equation
ClC1C=CC(C[C:7]([CH2:18][C:19]2([C:24]([NH:26][C@H:27]3[CH2:33][CH2:32][C:31]4[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=4[N:29]([CH2:38][C:39]([O:41]C(C)(C)C)=[O:40])[C:28]3=[O:46])=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20]2)([CH2:11][C:12]([NH:14][CH:15]([CH3:17])[CH3:16])=[O:13])[C:8]([O-:10])=[O:9])=CC=1.[C:49](O)([C:51](F)(F)F)=O.Cl[CH2:57][Cl:58]>>[Cl:58][C:57]1[CH:51]=[CH:49][C:11]([CH2:12][O:10][C:8]([CH:7]([CH2:11][C:12]([NH:14][CH:15]([CH3:16])[CH3:17])=[O:13])[CH2:18][C:19]2([C:24]([NH:26][C@H:27]3[CH2:33][CH2:32][C:31]4[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=4[N:29]([CH2:38][C:39]([OH:41])=[O:40])[C:28]3=[O:46])=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23]2)=[O:9])=[CH:7][CH:8]=1Participants
4
Procedure
318 g of the 4-chlorobenzyl-2-{[1-({[(3S)-1-(2-tert.butoxy-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}-carbonyl)cyclopentyl]methyl}-4-(isopropylamino)-4-oxobutyrate obtained above was dissolved in 11 ml dichloromethane, 1.08 ml TFA was added thereto and the mixture was stirred overnight. Then the solvent was largely evaporated at reduced pressure, the remaining residue was taken up in 10 ml EA and the organic phase was washed with water until it became pH-neutral. Then the solvent was evaporated again at reduced pressure and the remaining residue was fumed off once with 5 ml of toluene. 305 mg of the title compound was obtained as a white foam resin, MS: [M+H]+: 626/628; m/z: 657, 484, 425.
Workup
- customThen the solvent was largely evaporated at reduced pressure
- washthe organic phase was washed with water until it
- customThen the solvent was evaporated again at reduced pressure
Sources & evidence
- ORD record
- ord-b1ea0c1b963d4a4faf3d99a0855eb2a2
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07427611B2
Reaction notes
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