Dichloromethane → Diethylamino(benzyl)propanedioate trifluoroacetate

HRID 717315Notes

Reaction equation

HRID 717315 reaction equation
C([O:3][C:4](=[O:26])[C:5]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([NH:11][C:12](OC(C)(C)C)=O)[C:6]([O:8]CC)=[O:7])C.[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30].Cl[CH2:35]Cl>>[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30].[CH2:28]([N:11]([C:5]([CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:4]([OH:3])=[O:26])[C:6]([OH:8])=[O:7])[CH2:12][CH3:35])[CH3:29]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59685129Diethyl 2-benzyl-2-(tert-butoxycarbonylamino)malonate

Product 1

HCID 89500110Diethylamino(benzyl)propanedioate trifluoroacetate

Procedure

To the product of Step A (7.5 g, 20.52 mmol) in dichloromethane (24 mL) was added trifluoroacetic acid (12 mL, 156 mmol) and the mixture stirred for 1 h. The solvent was removed in vacuo and the oil azeotroped with toluene (2×20 mL) to afford the title compound as a tan amorphous solid. LC/MS 266.1 (M+1).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe oil azeotroped with toluene (2×20 mL)

Sources & evidence

ORD record
ord-ad7daaaed6774a9a9d9a229c510b17fb
Source dataset
uspto-grants-2015_11
Patent number
US09193717B2

Reaction notes

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