Trifluoroacetic acid → HCID 131714943, compound

HRID 1731396Notes

Reaction equation

HRID 1731396 reaction equation
CC(C)(OC(CN(C)C(N1CCC[C@H]1C(OCC1C=CC=CC=1)=O)=O)=O)C.FC(F)(F)C(O)=O.[C:35]1(OC)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[C:43]([CH2:46][CH2:47][N:48]([CH3:66])[C:49]([N:51]1[CH2:65][CH2:64][CH2:63][C@H:52]1[C:53]([O:55][CH2:56][C:57]1C=CC=CC=1)=[O:54])=[O:50])([OH:45])=[O:44]>>[C:43]([CH2:46][CH2:47][N:48]([CH3:66])[C:49]([N:51]1[CH2:65][CH2:64][CH2:63][C@H:52]1[C:53]([O:55][CH2:56][CH2:57][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:54])=[O:50])([OH:45])=[O:44]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 13657320HCID 13657320, compoundHCID 14129901HCID 14129901, compound

Product 1

HCID 131714943HCID 131714943, compound

Procedure

The ester product from part (c) (2.7 g., 7.17 mmole) is treated for 1.5 hours with 10 ml. of trifluoroacetic acid and 1.6 ml. of anisole. After concentrating to dryness it is triturated with ether-hexane. The crude material is crystallized from ether to yield 2 g. of 1-[[(2-carboxyethyl)methylamino]carbonyl]-L-proline, phenylmethyl ester; m.p. 102°-104°.

Workup

  1. concentrationAfter concentrating to dryness it
  2. customis triturated with ether-hexane
  3. customThe crude material is crystallized from ether
  4. customto yield 2 g

Sources & evidence

ORD record
ord-4aa8bac342764236b60cda2d6b989ea0
Source dataset
uspto-grants-1986_11
Patent number
US04621092

Reaction notes

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