2,6-Di-tert-butyl-4-methylpyridine → (S)-3-tert-Butoxycarbonylamino-4-methoxy-butyric acid benzyl ester

HRID 2104203Notes

Reaction equation

HRID 2104203 reaction equation
[CH2:1]([O:8][C:9]([CH2:11][C@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:13][OH:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C.F[B-](F)(F)F.C[O+](C)C>ClCCl>[CH2:1]([O:8][C:9]([CH2:11][C@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])[CH2:13][O:14][CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 10040985Phenylmethyl (3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-hydroxybutanoate

Product 1

HCID 57976545(S)-3-tert-Butoxycarbonylamino-4-methoxy-butyric acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To tert-butyl (S)-1-((benzyloxy)carbonyl)-3-hydroxypropan-2-ylcarbamate (1 eq.) in dichloromethane was added 2,6-di-t-butyl 4-methylpyridine (2.5 eq.) and trimethyloxonium tetrafluoroborate (1.25 eq.) at 0° C. The reaction mixture was gradually warm to room temperature and stirred overnight. The reaction mixture was diluted with dichloromethane and washed with cold satd. sodium bicarbonate, water, and brine and dried over sodium sulfate. Purification by silica gel chromatography (25% EtOAc/Hexane) provide pure product as a colorless viscous liquid.

Workup

  1. washwashed with cold satd
  2. dry with materialsodium bicarbonate, water, and brine and dried over sodium sulfate
  3. customPurification by silica gel chromatography (25% EtOAc/Hexane)
  4. customprovide pure product as a colorless viscous liquid

Sources & evidence

ORD record
ord-f370348922ca4d1da77958c5dd1a6921
Source dataset
uspto-grants-2009_08
Patent number
US07576221B2

Reaction notes

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