4-Chlorobenzaldehyde → HCID 68414055, compound

HRID 1662075Notes

Reaction equation

HRID 1662075 reaction equation
Cl.[CH2:2]([O:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:18]([NH:20][C@H:21]1[CH2:25][CH2:24][CH2:23][C@H:22]1[C:26]([O:28][CH2:29][C:30](=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:27])=[O:19])[NH2:17])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:38][C:39]1[CH:46]=[CH:45][C:42]([CH:43]=O)=[CH:41][CH:40]=1.C([O-])(=O)C.[Na+].[BH4-].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:2]([O:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:18]([NH:20][C@H:21]1[CH2:25][CH2:24][CH2:23][C@H:22]1[C:26]([O:28][CH2:29][C:30](=[O:37])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:27])=[O:19])[NH:17][CH2:43][C:42]1[CH:45]=[CH:46][C:39]([Cl:38])=[CH:40][CH:41]=1)=[O:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 5

HCID 77264-ChlorobenzaldehydeHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 4311764Sodium borohydrideHCID 68413119HCID 68413119, compound

Product 1

HCID 68414055HCID 68414055, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-oxo-2-phenylethyl (1R,2S)-2-({N5-[(benzyloxy)carbonyl]-L-ornithyl}amino)cyclopentanecarboxylate hydrochloride (0.30 g) and methylene chloride (6.0 ml) were added 4-chlorobenzaldehyde (87 mg), sodium acetate (53 mg), and sodium borohydride (215 mg) at room temperature, followed by stirring at room temperature over one night. To a reaction mixture was added a saturated sodium bicarbonate solution under ice-cooling to adjust the pH to about 7, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2-oxo-2-phenylethyl (1R,2S)-2-({N5-[(benzyloxy)carbonyl]-N2-(4-chlorobenzyl)-L-ornithyl}amino)cyclopentanecarboxylate (0.34 g).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7570568f66f74fe796088b453e37b5c4
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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