Hydrochloric Acid → HCID 86670075, compound

HRID 1024542Notes

Reaction equation

[C:1]([O:4][CH:5](SC)[C:6](=[O:30])[C@@H:7]([N:15]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2].CCO.[BH4-].[Na+].Cl>O.CCOC(C)=O>[C:1]([O:4][CH2:5][CH:6]([OH:30])[C@@H:7]([N:15]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: -20 °C

Procedure

To a suitable reactor was added 3c (2.2 g, 1.0 eq) and EtOH (11 mL) at 20-30° C. under N2. The mixture was cooled to −25 to −15° C., and NaBH4 (304.1 mg, 0.8 equiv) in H2O (4 mL) was added at below −15° C. The reaction mixture was warmed to −5-5° C. and stirred for 1 hr. The reaction was deemed complete as determined by TLC. 1N HCl aqueous solution (32 mL) was added at below 10° C., and the mixture was warmed to 20-30° C. EtOAc (200 mL) was added at 20-30° C., and the mixture was stirred at this temperature for 30 min. The separated organic portion was concentrated at 40-50° C. under reduced pressure to afford crude 4c. The diastereomeric ratio of crude 4c was determined to be 64/36 by HPLC analysis. The residue was purified by flash column chromatography (EtOAc/n-heptane=1/2) to give a diastereomeric mixture of 4c (2.20 g, 83% yield) as a yellow solid.

Workup

temperatureThe reaction mixture was warmed to −5-5° C.
temperaturethe mixture was warmed to 20-30° C
stirringthe mixture was stirred at this temperature for 30 min
concentrationThe separated organic portion was concentrated at 40-50° C. under reduced pressure

Sources & evidence

ORD record: ord-45cf6317843d4bf2bc881e4c0879b78e
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722921B2

Reaction notes

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