L-Proline → HCID 70083601, compound

HRID 1977584Notes

Reaction equation

[CH2:1]([O:3][C:4]([NH:6][C@@H:7]([C:14]([OH:16])=O)[CH2:8][CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:5])[CH3:2].[NH:17]1[CH2:24][CH2:23][CH2:22][C@H:18]1[C:19]([OH:21])=[O:20]>>[CH2:1]([O:3][C:4]([NH:6][C@@H:7]([C:14]([N:17]1[CH2:24][CH2:23][CH2:22][C@H:18]1[C:19]([OH:21])=[O:20])=[O:16])[CH2:8][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1)=[O:5])[CH3:2]

Participants

Reactant 2

HCID 145742L-Proline

HCID 70072198HCID 70072198, compound

Product 1

HCID 70083601HCID 70083601, compoundYield 71%

Procedure

2.43 g (10.5 mmol) of ethoxycarbonyl-3-cyclopentyl-D-alanine (Example 4, Step B) is treated according to the method described in Example 1, Step E, using proportional quantities of reagents and solvents. The resulting 2,4,5-trichlorophenylester is coupled with 1.15 g (10 mmol) of L-proline which yields 2.3 g (71%) of an oily product. Rf(6)=0.53.

Sources & evidence

ORD record: ord-3cabf9ef81bc40af9aebc4dc884b0186
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235707B1

Reaction notes

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