tert-Butanol → HCID 59753641, compound

HRID 751669Notes

Reaction equation

HRID 751669 reaction equation
[C:1]([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:21][C:22](O)([CH3:24])[CH3:23].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:22]([O:19][C:18](=[O:20])[C@@H:9]([NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=1)([CH3:24])([CH3:23])[CH3:21]

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 7020910N-(tert-Butoxycarbonyl)-4-fluoro-L-phenylalanine

Product 1

HCID 59753641HCID 59753641, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-N-Boc-4-fluorophenylalanine (2.83 g, 10.0 mmol), DMAP (0.12 g, 1.0 mmol) in DCM (20 mL) and 2-methyl-2-propanol (1.05 mL, 11.0 mmol), was added DCC (2.27 g, 11.0 mmol). The reaction mixture was stirred at rt for 16 h. The reaction mixture was filtered and washed several times with DCM. The filtrate was concentrated in vacuo and chromatographed on silica gel eluting with ethyl acetate:isohexane (1:4) to give the title compound. δH (CDCl3): 1.39 (9H, s), 1.41 (9H, s), 3.01 (2H, m), 4.41 (1H, m), 4.98 (1H, m), 6.95 (2H, m), 7.12 (2H, m).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed several times with DCM
  3. concentrationThe filtrate was concentrated in vacuo
  4. customchromatographed on silica gel eluting with ethyl acetate:isohexane (1:4)

Sources & evidence

ORD record
ord-7774d3b13c1046c8a9a9c6c2c7975266
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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