Thiazolidine → 1-[1-(2-indenylacetyl)-L-prolyl]-L-proline methyl ester

HRID 1086290Notes

Reaction equation

[CH:1]1([CH2:10][C:11]([N:13]2[CH2:20][CH2:19][CH2:18][C@H:14]2[C:15]([OH:17])=O)=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH3:21][O:22][C:23](=[O:29])[C@@H:24]1[CH2:28][CH2:27][CH2:26][NH:25]1.C1(CC(C2SCN[C@@H]2C(O)=O)=O)C2C(=CC=CC=2)CC1.S1CCNC1>>[CH3:21][O:22][C:23](=[O:29])[C@@H:24]1[CH2:28][CH2:27][CH2:26][N:25]1[C:15](=[O:17])[C@@H:14]1[CH2:18][CH2:19][CH2:20][N:13]1[C:11](=[O:12])[CH2:10][CH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

Reactant 4

HCID 10444Thiazolidine

HCID 853477Methyl L-prolinate

HCID 572056241-(2-indenylacetyl)-L-proline

HCID 1317169183-(2-indanylacetyl)-L-thioproline

Product 1

HCID 700486291-[1-(2-indenylacetyl)-L-prolyl]-L-proline methyl esterYield 75%

Procedure

A colorless oil of 1-[1-(2-indenylacetyl)-L-prolyl]-L-proline methyl ester was prepared in the same manner as in Example 1, except that 1-(2-indenylacetyl)-L-proline and L-proline methyl ester were used instead of 3-(2-indanylacetyl)-L-thioproline and thiazolidine, respectively (yield: 75%).

Sources & evidence

ORD record: ord-ea6e35473c774988b97fd8bf36fdf51b
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05028604

Reaction notes

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