Toluene → HCID 86620467, compound

HRID 561236Notes

Reaction equation

HRID 561236 reaction equation
C([O:3][C:4](=[O:17])[C@H:5]([CH2:13][C:14]([OH:16])=O)[NH:6][C:7](=[O:12])[C:8]([F:11])([F:10])[F:9])C.O=S(Cl)[Cl:20].[C:22]1([CH3:28])C=CC=CC=1>>[CH2:22]([N:6]([C:7](=[O:12])[C:8]([F:9])([F:10])[F:11])[C@H:5]([C:4]([OH:3])=[O:17])[CH2:13][C:14]([Cl:20])=[O:16])[CH3:28]

Participants

4

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 14353140HCID 14353140, compound

Product 1

HCID 86620467HCID 86620467, compound

Procedure

To a solution of N-(trifluoroacetyl)-L-aspartic acid α-ethyl ester (3 g, 11.7 mmol) in dry toluene (15 mL) was added SOCl2 (3 mL). After stirring at reflux for 1 h, the solution was cooled to rt. The mixture was filtered and the solid was washed with cold toluene. The solid was dried to afford the title compound. 1H NMR (400 MHz, CDCl3): δ4.71-4.75 (m, 1H), 4.28-2.36 (m, 2H), 3.64-3.70 (m, 1H), 3.56-3.61 (m, 1H), 1.31 (t, J=6 Hz, 3H).

Workup

  1. temperatureat reflux for 1 h
  2. filtrationThe mixture was filtered
  3. washthe solid was washed with cold toluene
  4. customThe solid was dried

Sources & evidence

ORD record
ord-00b3fb144cd54dec916b47752b2d7788
Source dataset
uspto-grants-2011_11
Patent number
US08063224B2

Reaction notes

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