Acetaldehyde → HCID 57700050, compound

HRID 1686011Notes

Reaction equation

HRID 1686011 reaction equation
[CH:1]1([O:6][C:7](=[O:41])[C@@H:8](N)[CH2:9][CH2:10][O:11][C:12]2[CH:21]=[C:20]3[C:15]([C:16]([O:22][C:23]4[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:37])[C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[CH:25][CH:24]=4)=[CH:17][CH:18]=[N:19]3)=[CH:14][C:13]=2[O:38][CH3:39])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:42](=O)[CH3:43].[C:45]([BH3-])#[N:46].[Na+].[CH3:49]O>C(O)(=O)C>[CH:1]1([O:6][C:7](=[O:41])[C@@H:8]([N:46]([CH2:45][CH3:49])[CH2:42][CH3:43])[CH2:9][CH2:10][O:11][C:12]2[CH:21]=[C:20]3[C:15]([C:16]([O:22][C:23]4[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:37])[C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[CH:25][CH:24]=4)=[CH:17][CH:18]=[N:19]3)=[CH:14][C:13]=2[O:38][CH3:39])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 11949608HCID 11949608, compound

Product 1

HCID 57700050HCID 57700050, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

To (S)-2-Amino-4-[4-(4-benzoylamino-phenoxy)-6-methoxy-quinolin-7-yloxy]-butyric acid cyclopentyl ester (37 mg, 0.066 mmol) in anhydrous methanol (1 ml) were added acetaldehyde (4.1 μL, 0.073 mmol) and 1 drop of acetic acid. The reaction mixture was stirred at room temperature for 3 hours. Sodium cyanoborohydride (10.3 mg, 0.165 mmol) was then added and the reaction was left stirring overnight at room temperature, prior to concentration under vacuum. Purification was achieved on a prepacked Si-column followed by preparative HPLC, to provide the title compound as a di-TFA salt (10 mg, 18% yield)

Workup

  1. waitthe reaction was left
  2. stirringstirring overnight at room temperature
  3. concentrationto concentration under vacuum
  4. customPurification

Sources & evidence

ORD record
ord-f492d140413a47dd8e772b10172e231e
Source dataset
uspto-grants-2012_04
Patent number
US08148531B2

Reaction notes

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