Hydrochloric Acid → HCID 23251676, compound
Reaction equation
[CH2:1]([O:8][C:9](=[O:24])[CH:10]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:11][CH2:12][C:13](O)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(Cl)=O)C.[BH4-].[Na+].Cl>C1COCC1.O>[CH2:1]([O:8][C:9](=[O:24])[CH:10]([NH:16][C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:11][CH2:12][CH2:13][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
The 2-tert-butoxycarbonylamino-pentanedioic acid 1-benzyl ester (4.06 g, 12 mmol) and TEA (5 mL, 35.87 mmol) were dissolved in THF (60 mL) and cooled to 0° C. Ethylchloroformate (3.4 mL, 35.7 mmol) was added dropwise. The mixture was stirred at 0° C. for 5 minutes and warmed to r.t. for 1 h. NaBH4 (1.88 g, 49.7 mmol) was added followed by addition of 1 drop of H2O. The reaction mixture was stirred at r.t. overnight. 4 N HCl was added at 0° C. and extracted with EtOAc (100 mL). The aqueous layer was washed with H2O (100 mL), NaOH (2×100 mL), H2O (100 mL) and brine (100 mL). The organic layer was dried with Na2SO4, filtered, and concentrated. The crude product was purified by combi-flash to give 2.89 g of 2-tert-butoxycarbonylamino-5-hydroxy-pentanoic acid benzyl ester in 75% yield.
Workup
- temperaturewarmed to r.t. for 1 h
- stirringThe reaction mixture was stirred at r.t. overnight
- extractionextracted with EtOAc (100 mL)
- washThe aqueous layer was washed with H2O (100 mL), NaOH (2×100 mL), H2O (100 mL) and brine (100 mL)
- dry with materialThe organic layer was dried with Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was purified by combi-flash
Sources & evidence
- ORD record
- ord-00fe12ce2d874490b84dde1d698bf087
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08586744B2
Reaction notes
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