4-Methylmorpholine → HCID 57035141, compound
Reaction equation
C[CH:2]([S:4][CH2:5][C:6]([OH:8])=O)[CH3:3].[CH3:9]N1CCOCC1.C(OC(Cl)=O)C(C)C.[NH2:24][CH2:25][CH2:26][C@H:27]([OH:44])[C@@H:28]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>C1COCC1.C(OCC)(=O)C>[CH2:2]([S:4][CH2:5][C:6]([NH:24][CH2:25][CH2:26][C@H:27]([OH:44])[C@@H:28]([NH:36][C:37]([O:39][C:40]([CH3:41])([CH3:43])[CH3:42])=[O:38])[CH2:29][CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1)=[O:8])[CH2:3][CH3:9]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
To (2-propylmercapto)acetic acid (44.3 mg, 0.33 mmol) in the THF (3 mL) at 0°(b) was added N-methylmorpholine (37 microliters, 0.34 mmol) followed by isobutylchloroformate (43 microliters, 0.33 mmol). The mixture was stirred at 0° C. for 15 minutes and (3S,4S)-1-amino-3-hydroxy-4-t-butyloxycarbonylamino-5-cyclohexylpentane (51.0 mg, 0.17 mmol) was added followed by stirring at 0° C. for 15 minutes and at 25° C. for 2 hours. The mixture was poured into ethyl acetate, washed with 0.5 M H3PO4, 2 M Na2SO4 and evaporated to afford 36 mg (50%) of the desired compound. Mass spectrum: (M+1)+ =417.
Workup
- stirringby stirring at 0° C. for 15 minutes and at 25° C. for 2 hours
- washwashed with 0.5 M H3PO4, 2 M Na2SO4
- customevaporated
Sources & evidence
- ORD record
- ord-13a984ef6b20457abac97b0ce9572ef8
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04857507
Reaction notes
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