4-Methoxybenzaldehyde → HCID 67374585, compound

HRID 1677010Notes

Reaction equation

HRID 1677010 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][NH:5][S:6]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Br:18])[CH:16]=2)[N:11]([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[C:10]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29])(=[O:8])=[O:7].[CH3:33][O:34][C:35]1[CH:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][CH:36]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.CCOC(C)=O>[Br:18][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]([S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20])[C:10]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:9]2[S:6]([NH:5][CH2:4][CH2:3][NH:2][CH2:39][C:38]1[CH:41]=[CH:42][C:35]([O:34][CH3:33])=[CH:36][CH:37]=1)(=[O:8])=[O:7]

Participants

6

Reactant 3

HCID 312444-MethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67373781HCID 67373781, compound

Product 1

HCID 67374585HCID 67374585, compound

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 89, Step A was combined with 1.2 equivalents of 4-methoxybenzaldehyde and 1.5 equivalent of sodium triacetoxyborohydride in dichloroethane. The reaction was stirred for 1.5 hours at room temperature, was diluted with EtOAc and washed with sat. NaHCO3 and brine. The solution was dried with Na2SO4 and concentrated in vacuo to give the titled compound. ESI+ MS: 651 [M+H]+.

Workup

  1. washwashed with sat. NaHCO3 and brine
  2. dry with materialThe solution was dried with Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0d07fe84772b4ba3891f5c48f759cac5
Source dataset
uspto-grants-2011_08
Patent number
US08008295B2

Reaction notes

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