Diisopropylcarbodiimide → Tert-butyl 1-((4-(1-phenylcyclohexyl)phenoxy)carbonyl)-2-methylpropylcarbamate

HRID 70729Notes

Reaction equation

HRID 70729 reaction equation
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:20]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:21]([C:25](O)=[O:26])[CH:22]([CH3:24])[CH3:23].CC(C)N=C=NC(C)C>C1COCC1.CN(C1C=CN=CC=1)C>[C:1]1([C:7]2([C:13]3[CH:14]=[CH:15][C:16]([O:19][C:25]([CH:21]([NH:20][C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:34])[CH3:33])[CH:22]([CH3:24])[CH3:23])=[O:26])=[CH:17][CH:18]=3)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 83693Boc-L-ValineHCID 15384544-(1-Phenylcyclohexyl)phenol

Product 1

HCID 66967822Tert-butyl 1-((4-(1-phenylcyclohexyl)phenoxy)carbonyl)-2-methylpropylcarbamate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred solution at room temperature of 4-(1-phenylcyclohexyl)phenol (311 mg, 1.23 mmol) in dry THF (2 mL) was added BocValOH (295 mg, 1.36 mmol) dissolved in THF (2 mL). A solution of DIC (231 μL; 1.48 mmol) in THF (2 mL) was added drop wise, which caused precipitation after a few minutes. After 5 min DMAP (166 mg; 1.36 mmol) was added and stirring was continued for 19 h. The reaction mixture was concentrated in vacuo and purified by flash chromatography (eluent: EtOAc (0-10%) in heptane) affording 517 mg (1.14 mmol; 93%) of colourless oil. LC-MS purity (UV/MS): 100/100%, Rt 6.77 min, M+18: 469.53.

Workup

  1. customprecipitation after a few minutes
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified by flash chromatography (eluent: EtOAc (0-10%) in heptane)
  4. customaffording 517 mg (1.14 mmol; 93%) of colourless oil

Sources & evidence

ORD record
ord-c6d317735b2344efb16480c76fdf15f4
Source dataset
uspto-grants-2014_09
Patent number
US08822548B2

Reaction notes

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