Benzaldehyde → HCID 67275341, compound

HRID 1696945Notes

Reaction equation

HRID 1696945 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[N:10][C:11]([N:18]3[CH2:22][CH:21]([OH:23])[CH:20]([NH2:24])[CH2:19]3)=[C:12]([F:17])[CH:13]=2)[N:8]([CH2:25][CH2:26][C:27]#[N:28])[CH:7]=1)=[O:5])[CH3:2].[CH:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.C(O)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[N:10][C:11]([N:18]3[CH2:22][CH:21]([OH:23])[CH:20]([NH:24][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH2:19]3)=[C:12]([F:17])[CH:13]=2)[N:8]([CH2:25][CH2:26][C:27]#[N:28])[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67275567HCID 67275567, compound

Product 1

HCID 67275341HCID 67275341, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

A solution of EXAMPLE 199A (0.12 g) and benzaldehyde (0.063 mL) in methanol (10 mL) and acetic acid (2 drops) was stirred for 30 minutes at 25° C., treated with sodium triacetoxyborohydride (0.196 g), stirred for 18 hours, and concentrated; and the concentrate chromatographed on silica gel with 5% methanol/dichloromethane.

Workup

  1. concentrationconcentrated
  2. customand the concentrate chromatographed on silica gel with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-778b7ed1793d4684a3b859e05071c41a
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

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