Trityl chloride → Methyl trityl-D-serinate

HRID 1425924Notes

Reaction equation

HRID 1425924 reaction equation
[NH2:1][C@@H:2]([C:5]([O:7][CH3:8])=[O:6])[CH2:3][OH:4].[C:9](Cl)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)Cl>[OH:4][CH2:3][C@@H:2]([NH:1][C:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 90387Methyl D-serinate

Product 1

HCID 7438296Methyl trityl-D-serinateYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of D-Ser-OMe (LXXXVIII) in dry DCM was added TEA (1.2 eq). After the solution became clear, trityl chloride (1 eq in dry DCM) was added dropwise and stirred for 2 hours. The reaction mixture was washed with 2M HCl, brine and dried over anhydrous MgSO4. The solvent was removed under reduced pressure to give the crude product as a colorless oil. The oil crystallized from Et2O/hexane to produce pure (R)-methyl 3-hydroxy-2-(tritylamino)propanoate (LXXXIX) as white solid (85% yield).

Workup

  1. washThe reaction mixture was washed with 2M HCl, brine
  2. dry with materialdried over anhydrous MgSO4
  3. customThe solvent was removed under reduced pressure
  4. customto give the crude product as a colorless oil
  5. customThe oil crystallized from Et2O/hexane

Sources & evidence

ORD record
ord-5923fe6caf804861add83c9277ed5255
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

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