Hydrochloric Acid → S-[4-(9-Fluorenylmethoxy)-4-oxobutyl]-L-cysteine
Reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:21])[CH2:17][CH2:18][CH2:19]Br)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH2:22][C@H:23]([C:26]([OH:28])=[O:27])[CH2:24][SH:25].CCN(C(C)C)C(C)C.Cl>C(O)C.O>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:21])[CH2:17][CH2:18][CH2:19][S:25][CH2:24][C@@H:23]([C:26]([OH:28])=[O:27])[NH2:22])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1Participants
6
Procedure
The title compound of example 1 (3.0 g, 8.72 mmol) was added to a solution of L-cysteine (1.0 g, 8.26 mmol) and DIEA (4.4 mL, 24.7 mmol) in EtOH-H2O (1:1, 100 mL). The resulting heterogeneous mixture was stirred vigorously at room temperature (20°-22° C.) for 18 h. The mixture was rendered acidic by the addition of 1N HCl (ph=6). The solid in the reaction mixture was collected on a filter and washed with H2O and EtOH. A suspension of the solid in EtOH (70 mL) was heated with stirring then allowed to cool. The solid in the suspension was collected on a filter, washed with EtOH, Et2O and dried to give the title compound (1.2 g).
Workup
- customThe solid in the reaction mixture was collected on
- filtrationa filter
- washwashed with H2O and EtOH
- additionA suspension of the solid in EtOH (70 mL)
- temperaturewas heated
- stirringwith stirring
- temperatureto cool
- customThe solid in the suspension was collected on a filter
- washwashed with EtOH, Et2O
- customdried
Sources & evidence
- ORD record
- ord-adce63b78ad74900b8368867dc397e00
- Source dataset
- uspto-grants-1990_01
- Patent number
- US04891358
Reaction notes
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