Sodium borohydride → HCID 87192989, compound

HRID 216297Notes

Reaction equation

HRID 216297 reaction equation
[C:1]([C:4]1[N:9]=[C:8]([CH2:10][N:11]2[CH2:15][CH2:14][N:13]([C@@H:16]([C:48]([CH3:51])([CH3:50])[CH3:49])[C:17]([NH:19][C@@H:20]([CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C@H:21]([OH:40])[CH2:22][N:23]([S:28]([C:31]3[CH:36]=[CH:35][C:34](/[CH:37]=[N:38]/[OH:39])=[CH:33][CH:32]=3)(=[O:30])=[O:29])[CH2:24][CH:25]([CH3:27])[CH3:26])=[O:18])[C:12]2=[O:52])[CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[CH2:41]([C@H:20]([NH:19][C:17](=[O:18])[C@@H:16]([N:13]1[CH2:14][CH2:15][N:11]([CH2:10][C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([CH:1]([OH:3])[CH3:2])[N:9]=2)[C:12]1=[O:52])[C:48]([CH3:50])([CH3:51])[CH3:49])[C@H:21]([OH:40])[CH2:22][N:23]([S:28]([C:31]1[CH:32]=[CH:33][C:34](/[CH:37]=[N:38]/[OH:39])=[CH:35][CH:36]=1)(=[O:30])=[O:29])[CH2:24][CH:25]([CH3:27])[CH3:26])[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 87193464HCID 87193464, compound

Product 1

HCID 87192989HCID 87192989, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of the product of Example 288A (86 mg) in methanol (1.5 mL) was treated with NaBH4 (8.8 mg, 2 equivalents) at 0° C. The mixture was stirred for 1 h at 25° C. and quenched by adding acetone (0.2 mL). The solvents were evaporated, and the residue was purified using 7% methanol/dichloromethane to give 83 mg (96%) of the title compound.

Workup

  1. customquenched
  2. additionby adding acetone (0.2 mL)
  3. customThe solvents were evaporated
  4. customthe residue was purified

Sources & evidence

ORD record
ord-ac4bffdb94f14bf494995dcbca777e43
Source dataset
uspto-grants-2012_06
Patent number
US08193227B2

Reaction notes

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