Sodium borohydride → N-(7-hydroxymethyl-chroman-4-yl)-3-(naphthalen-2-yl-sulfonylamino)-3-phenyl-propionamide

HRID 32055Notes

Reaction equation

[CH:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([NH:13][C:14](=[O:37])[CH2:15][CH:16]([NH:23][S:24]([C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=3)(=[O:26])=[O:25])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:8][CH2:9][O:10]2)=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+]>C1COCC1.CO>[OH:2][CH2:1][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([NH:13][C:14](=[O:37])[CH2:15][CH:16]([NH:23][S:24]([C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=3)(=[O:26])=[O:25])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:8][CH2:9][O:10]2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

N-(7-Formyl-chroman-4-yl)-3-(naphthalen-2-yl-sulfonylamino)-3-phenyl-propionamide (Example 1, Step G) (1.83 g, 3.56 mmol) was dissolved in a 1:1 solution of THF and MeOH (100 mL). The solution was cooled to 0° C. and NaBH4 (0.135 g, 3.56 mmol) was added. The reaction was stirred for 30 min. The volatiles were removed in vacuo and the resulting residue was dissolved in EtOAc and washed sequentially with a saturated NaHCO3 solution and brine. The aqueous phases were extracted once with EtOAc. The organic phases were combined, dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound. MS (ESI) m/z 517 (M+H)+.

Workup

customThe volatiles were removed in vacuo
dissolutionthe resulting residue was dissolved in EtOAc
washwashed sequentially with a saturated NaHCO3 solution and brine
extractionThe aqueous phases were extracted once with EtOAc
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f954f9624efc4e64bac723edcd33ca3e
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425631B2

Reaction notes

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