Dichloromethane → 2-(R)-(2-Acetoxymethyl-4-amino-3-methyl-benzyl)-succinic acid diethyl ester

HRID 1985477Notes

Reaction equation

HRID 1985477 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=[O:4].[CH2:8]([O:10][C:11](=[O:40])[C@@H:12]([CH:19](COC(=O)C)[C:20]1[CH:25]=[CH:24][C:23]([NH:26]C(OC(C)(C)C)=O)=[C:22]([CH3:34])[CH:21]=1)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:9].Cl[CH2:42]Cl>>[CH2:8]([O:10][C:11](=[O:40])[C@H:12]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[C:22]([CH3:34])[C:21]=1[CH2:42][O:5][C:3](=[O:4])[CH3:2])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:9]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 673178612-(R)-(acetoxymethyl-4-tert-butoxycarbonylamino-3-methyl-benzyl)-succinic acid diethyl ester

Product 1

HCID 597320262-(R)-(2-Acetoxymethyl-4-amino-3-methyl-benzyl)-succinic acid diethyl esterYield 99%

Procedure

Trifluoroacetic acid (2.5 mL) was added to a solution of 2-(R)-(acetoxymethyl-4-tert-butoxycarbonylamino-3-methyl-benzyl)-succinic acid diethyl ester (525 mg, 1.1 mmol) in dichloromethane (10 mL). Reaction mixture was stirred at room temperature for 1 hour. Mixture was concentrated in vacuo. Residue was treated with aqueous sodium bicarbonate and extracted with ethyl acetate (2×20 mL). Combined organic layers were dried (magnesium sulfate), filtered and concentrated in vacuo. The title compound was obtained as amber oil in 99% yield. MS m/e (M−C2H4O2+H)+=306.1.

Workup

  1. customReaction mixture
  2. concentrationMixture was concentrated in vacuo
  3. additionResidue was treated with aqueous sodium bicarbonate
  4. extractionextracted with ethyl acetate (2×20 mL)
  5. dry with materialCombined organic layers were dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8e9af3a19dd54cc3abfdd9bc463c0bb5
Source dataset
uspto-grants-2009_06
Patent number
US07544680B2

Reaction notes

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