1,2-Dichloroethane → Carbamic acid, [(1S)-2,2-dimethyl-1-[[(2-pyridinylmethyl)amino]carbonyl]propyl]-, 1,1-dimethylethyl ester

HRID 565249Notes

Reaction equation

HRID 565249 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.[CH:21]1[CH:22]=[CH:23][C:24]2[N:29](O)N=[N:27][C:25]=2[CH:26]=1.N1C=CC=CC=1CN>ClCCl>[N:27]1[CH:23]=[CH:22][CH:21]=[CH:26][C:25]=1[CH2:24][NH:29][C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 195092-PyridinemethanamineHCID 757711-HydroxybenzotriazoleHCID 2734668(S)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid

Product 1

HCID 70237877Carbamic acid, [(1S)-2,2-dimethyl-1-[[(2-pyridinylmethyl)amino]carbonyl]propyl]-, 1,1-dimethylethyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of (2S)-2-tert-butoxycarbonylamino-3,3-dimethylbutanoic acid (11.6 g, 50 mmol) in dichloromethane (100 mL) is added EDC (14.4 g, 75 mmol), HOBT (7.65 g, 50 mmol), and 2-pyridylmethylamine (6.48 g, 60 mmol). The resulting solution is stirred at 25° C. for 18 h, then diluted with dichloromethane (200 mL) and washed with 2 M hydrochloric acid and 2 M sodium hydroxide. The organic layer is dried over anhydrous magnesium sulfate and concentrated in vacuo to provide (2S)-2-tert-butoxycarbonylamino-3,3-dimethylbutanoic acid 2-pyridylmethylamide as a white solid (16 g, 100% yield).

Workup

  1. washwashed with 2 M hydrochloric acid and 2 M sodium hydroxide
  2. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0f8a8fc245ee49faa22b6ef0e1b5898c
Source dataset
uspto-grants-2001_01
Patent number
US06172064B2

Reaction notes

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