tert-Butanol → 4-Benzyloxycarbonylamino-cyclohexanecarboxylic acid tert-butyl ester

HRID 444710

Reaction equation

HRID 444710 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=[O:19])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21](O)([CH3:24])([CH3:23])[CH3:22].CC(C)N=C=NC(C)C>C(Cl)Cl.CN(C=O)C.CN(C1C=CN=CC=1)C>[C:21]([O:19][C:18]([CH:15]1[CH2:16][CH2:17][CH:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:13][CH2:14]1)=[O:20])([CH3:24])([CH3:23])[CH3:22]

Participants

7

Reactant 3

HCID 6386tert-ButanolHCID 12734DiisopropylcarbodiimideHCID 2852474-(((Benzyloxy)(hydroxy)methylidene)amino)cyclohexane-1-carboxylic acid

Product 1

HCID 538881934-Benzyloxycarbonylamino-cyclohexanecarboxylic acid tert-butyl esterYield 54.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-benzyloxycarbonylamino-cyclohexanecarboxylic acid (8.0 g, 28.78 mmol) in DCM (35 mL) and DMF (35 mL) is added t-butanol (10 mL, 105.4 mmol) and DMAP (1.4 g, 11.50 mmol). DIPC (10 mL) is added portionwise over 1 h. The resulting mixtures stirs 18 h. The mixture is mounted onto SiO2 and purified by flash chromatography (gradient elution: 0-60% EtOAc/Hep) which affords 5.2 g of 4-benzyloxycarbonylamino-cyclohexanecarboxylic acid tert-butyl ester. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.14 (m, 2 H) 1.30 (m, 2 H) 1.38 (m, 9 H) 1.82 (m, 4 H) 2.07 (m, 1 H) 3.20 (m, 1 H) 3.47 (m, 3 H) 4.99 (m, 2 H) 7.27 (m, 5 H).

Workup

  1. customThe resulting mixtures stirs 18 h
  2. custompurified by flash chromatography (gradient elution: 0-60% EtOAc/Hep) which

Sources & evidence

ORD record
ord-64d3637cf11f405ebc08fa57c9171a4e
Source dataset
uspto-grants-2013_07
Patent number
US08476224B2

Linked notes

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