N-(tert-butoxycarbonyl)glycine → HCID 69630702, compound

HRID 1792850Notes

Reaction equation

HRID 1792850 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][NH2:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][C:14](O)=[O:15]>O1CCOCC1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>[C:20]([O:19][C:17](=[O:18])[NH:12][CH2:13][C:14](=[O:15])[NH:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 2

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 83242Benzenebutanamine

Product 1

HCID 69630702HCID 69630702, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 11430Potassium CarbonateSolventHCID 312751,4-DioxaneSolvent

Procedure

Phenylbutylamine (8.2 g, 52 mmol) is added to a mixture of BOC-Gly-PNB (14.82 g, 50 mmol) in dioxane (60 mL) and 1 M K2CO3 (60 mL). The mixture is stirred 16 h and then diluted with CH2Cl2 and washed with a saturated NaHCO3 solution until the organic phase is colorless. The organics are dried (MgSO4) and concentrated to provide [(4-phenyl-butylcarbamoyl)-methyl]-carbamic acid tert-butyl ester which is used as is without further purification.

Workup

  1. washwashed with a saturated NaHCO3 solution until the organic phase
  2. dry with materialThe organics are dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-403720b4bef8437f92fc3e9aee7e95fe
Source dataset
uspto-grants-2006_07
Patent number
US07078425B2

Reaction notes

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