Acetic Acid → HCID 89498315, compound

HRID 1430267Notes

Reaction equation

HRID 1430267 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[N:28]=[C:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:26]([C:36]3[CH:37]=[C:38]4[C:43](=[CH:44][CH:45]=3)[CH2:42][NH:41][CH2:40][CH2:39]4)=[CH:25][CH:24]=1)[CH2:19][CH2:18]2)=[O:12].[CH:46](=O)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.C(O)(=O)C.CO>ClCCl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[N:28]=[C:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:26]([C:36]3[CH:37]=[C:38]4[C:43](=[CH:44][CH:45]=3)[CH2:42][N:41]([CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[CH2:40][CH2:39]4)=[CH:25][CH:24]=1)[CH2:19][CH2:18]2)=[O:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 887MethanolHCID 89498204HCID 89498204, compound

Product 1

HCID 89498315HCID 89498315, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of EXAMPLE 133A (20 mg), benzaldehyde (6.58 μL), MP-CNBH3 (100 mg, 2.47 mmol/g), acetic acid (2 μL) in dichloromethane (2 mL)/methanol (2 mL) was shaken at room temperature for 18 hours. The reaction mixture was filtered, washed with methanol/dichloromethane, concentrated and purified by RP HPLC(C8, 30-100% CH3CN/water/0.1% TFA) to provide the title compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with methanol/dichloromethane
  3. concentrationconcentrated
  4. custompurified by RP HPLC(C8, 30-100% CH3CN/water/0.1% TFA)

Sources & evidence

ORD record
ord-21835eb0ce6041d881735dd76ec3f854
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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