Pivalaldehyde → 1,1-Dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-[(2,2-dimethylpropyl)amino]butanoate

HRID 1160412Notes

Reaction equation

HRID 1160412 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[NH2:15][CH2:16][C@@H:17]([NH:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[C:29]([Cl:35])[CH:28]=1)[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].[CH3:36][C:37]([CH3:41])([CH3:40])[CH:38]=O>C(Cl)Cl>[Cl:35][C:29]1[CH:28]=[C:27]([NH:26][C@H:17]([CH2:16][NH:15][CH2:36][C:37]([CH3:41])([CH3:40])[CH3:38])[CH2:18][C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH:32]=[CH:31][C:30]=1[C:33]#[N:34]

Participants

5

Reactant 3

HCID 12417PivalaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 595161531,1-Dimethylethyl (3S)-4-amino-3-[(3-chloro-4-cyanophenyl)amino]butanoate

Product 1

HCID 595161681,1-Dimethylethyl (3S)-3-[(3-chloro-4-cyanophenyl)amino]-4-[(2,2-dimethylpropyl)amino]butanoateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

NaBH(OAc)3 (0.5 g, 2.32 mmol) was added to a solution of 1,1-dimethylethyl (3S)-4-amino-3-[(3-chloro-4-cyanophenyl)amino]butanoate (0.48 g, 1.55 mol), and trimethylacetaldehyde (0.14 g, 1.60 mmol) in CH2Cl2 (35 mL). After stirring at room temperature for 2 h, the reaction was diluted with CH2Cl2 (35 mL), washed with saturated NaHCO3, dried over Na2SO4, filtered, and concentrated to yield the titled product (0.575 g, 98%) as an oil. LC-MS (ES) m/e 380.6 (M+H)+.

Workup

  1. washwashed with saturated NaHCO3
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7f2788a5bdaf4e9e96c7d56d59de37b7
Source dataset
uspto-grants-2010_10
Patent number
US07816395B2

Reaction notes

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