1,2-Dichloroethane → 2-(Tert-butoxycarbonylamino)-4-methylpentyl 4-bromobutanoate

HRID 1776972Notes

Reaction equation

HRID 1776972 reaction equation
[OH:1][CH2:2][CH:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH:5]([CH3:7])[CH3:6].[Br:16][CH2:17][CH2:18][CH2:19][C:20](O)=[O:21].C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:16][CH2:17][CH2:18][CH2:19][C:20]([O:1][CH2:2][CH:3]([NH:8][C:9]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:15])[CH2:4][CH:5]([CH3:7])[CH3:6])=[O:21]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 758094-Bromobutyric acidHCID 546110tert-butyl N-(1-hydroxy-4-methylpentan-2-yl)carbamate

Product 1

HCID 866410002-(Tert-butoxycarbonylamino)-4-methylpentyl 4-bromobutanoateYield 97.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl 1-hydroxy-4-methylpentan-2-ylcarbamate (2.00 g, 9.20 mmol) and 4-bromo-butyric acid (2.57 g, 15.38 mmol) were dissolved in CH2Cl2 (40 ml) and the mixture was cooled to 0° C. EDC (4.20 g, 21.90 mmol) and DMAP (0.27 g, 2.21 mmol) were added and the reaction was slowly warmed to room temperature and stirred overnight. Then the reaction was treated with a solution of 5% aqueous NaH2PO4 (100 ml). The organic layer was washed with a solution of 10% aqueous Na2CO3 (100 ml) and brine, dried over Na2SO4, filtered and concentrated. The obtained crude clear oil corresponding to the title compound (3.30 g) was used without any further purification.

Workup

  1. temperaturethe reaction was slowly warmed to room temperature
  2. washThe organic layer was washed with a solution of 10% aqueous Na2CO3 (100 ml) and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-255b1613995b4bd8b58083ebab237f3c
Source dataset
uspto-grants-2016_02
Patent number
US09266820B2

Reaction notes

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