3-Methylbutanal → HCID 54287955, compound

HRID 1069448Notes

Reaction equation

HRID 1069448 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([CH2:30][CH:31]=[C:32]([CH3:34])[CH3:33])[CH2:16][C:17]([NH:20][C:21](=[O:29])[C@@H:22]([NH:27][CH3:28])[CH2:23][CH:24]([CH3:26])[CH3:25])([CH3:19])[CH3:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)[CH2:36][CH:37]([CH3:39])[CH3:38].[BH-](OC(C)=O)(OC(C)=O)O[C:43](C)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([CH2:30][CH:31]=[C:32]([CH3:33])[CH3:34])[CH2:16][C:17]([NH:20][C:21](=[O:29])[C@@H:22]([N:27]([CH3:43])[CH2:28][CH2:36][CH:37]([CH3:39])[CH3:38])[CH2:23][CH:24]([CH3:26])[CH3:25])([CH3:19])[CH3:18])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 115523-MethylbutanalHCID 5049666Sodium triacetoxyborohydrideHCID 53989020HCID 53989020, compound

Product 1

HCID 54287955HCID 54287955, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(S)-4-Methyl-2-methylamino-pentanoic acid {2-[(4-benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-1,1-dimethyl-ethyl}-amide (XIa, 0.67 mmol) was dissolved in CH2Cl2 (10 mL), treated with isovaleraldehyde (60.2 mg, 0.7 mmol), and stirred for 30 minutes. The reaction was cooled to 0° C. and NaBH(OAc)3 (212 mg, 1 mmol) was added. The mixture was stirred at room temperature for 15 hours, then washed with saturated sodium bicarbonate solution and concentrated. The residue was chromatographed on silica gel eluting with 4:1 hexane/EtOAc to give the desired product.

Workup

  1. stirringThe mixture was stirred at room temperature for 15 hours
  2. washwashed with saturated sodium bicarbonate solution
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel eluting with 4:1 hexane/EtOAc

Sources & evidence

ORD record
ord-c741d86e873d4396898ff66e236589fc
Source dataset
uspto-grants-2001_06
Patent number
US06251918B1

Reaction notes

Loading…