Methanol → HCID 68926983, compound

HRID 32086Notes

Reaction equation

[BH4-].[Li+].C[O:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]2[CH:15]([NH:16][C:17](=[O:40])[CH2:18][CH:19]([NH:26][S:27]([C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=3)(=[O:29])=[O:28])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:14][S:13](=[O:42])(=[O:41])[N:12]([CH3:43])[C:11]=2[CH:44]=1)=O.CO>C1COCC1>[OH:4][CH2:5][C:7]1[CH:8]=[CH:9][C:10]2[CH:15]([NH:16][C:17](=[O:40])[CH2:18][CH:19]([NH:26][S:27]([C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=3)(=[O:29])=[O:28])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:14][S:13](=[O:41])(=[O:42])[N:12]([CH3:43])[C:11]=2[CH:44]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Lithium borohydride (10.0 mL, 20 mmol, 2.0 M in THF) was added to a THF (50 mL) solution of 4-(3-(naphthalen-2-yl-sulfonylamino)-3-phenyl-propionylamino)-1-methyl-2,2-dioxo-1,2,3,4-tetrahydro-2λ6-benzo[c][1,2]thiazine-7-carboxylic acid methyl ester (Step C) (1.76 g, 2.9 mmol). Following addition of MeOH (0.3 mL, 8 mmol), the mixture was stirred for 20 h at 50° C. The reaction was quenched with acetone, MeOH and dilute HCl at 0° C. The mixture was diluted with CH2Cl2 (400 mL), washed with H2O, dried over MgSO4, filtered, and concentrated in vacuo. Chromatography on silica (0-5% MeOH in CH2Cl2) provided the title compound. MS (−APCI, m/z): 578 (M−H)−.

Workup

customThe reaction was quenched with acetone, MeOH and dilute HCl at 0° C
additionThe mixture was diluted with CH2Cl2 (400 mL)
washwashed with H2O
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8e231a3a812d448ab4cf171cac7e836f
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425631B2

Reaction notes

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