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

HRID 2361578Notes

Reaction equation

HRID 2361578 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, 2H) 1.30 (m, 2H) 1.38 (m, 9H) 1.82 (m, 4H) 2.07 (m, 1H) 3.20 (m, 1H) 3.47 (m, 3H) 4.99 (m, 2H) 7.27 (m, 5H).

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-5b99d01e798e4d879c9c0680f8f078bb
Source dataset
uspto-grants-2014_04
Patent number
US08691756B2

Reaction notes

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