HCID 66916587, compound → HCID 91380141, compound

HRID 1009828Notes

Reaction equation

HRID 1009828 reaction equation
[CH:1]([O:14][C:15]([CH:17]1[CH2:21][C@@H:20]([C:22](=[O:24])[CH3:23])[CH:19]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH2:34][CH2:35][CH2:36][O:37][CH3:38])[CH:26]=2)[NH:18]1)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(=O)C/N=C/C1C=CC(OC)=C(OCCCOC)C=1)(C1C=CC=CC=1)C1C=CC=CC=1>>[CH:1]([O:14][C:15]([CH:17]1[CH2:21][C@H:20]([C:22](=[O:24])[CH3:23])[CH:19]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH2:34][CH2:35][CH2:36][O:37][CH3:38])[CH:26]=2)[NH:18]1)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 66916587HCID 66916587, compoundHCID 178495367HCID 178495367, compound

Product 1

HCID 91380141HCID 91380141, compound

Procedure

In a similar fashion 4(R)-Acetyl-5-[4-methoxy-3-(3-methoxy-propoxy)-phenyl]-pyrrolidine-2-carboxylic acid benzhydryl ester, IVa is prepared as a racemate from {[1-[4-Methoxy-3-(3-methoxy-propoxy)-phenyl]-meth-(E)-ylidene]-amino}-acetic acid benzhydryl ester. 1H-NMR, δ CDCl3: 7.45-7.25 (10H, m, Ph), 7.01 (1H, Brs, NH), 6.80 (3H, m, Ph), 4.55 (1H, d, NCHCO), 4.10-4.03 (3H, m, CH2O), 3.45 (1H, q, CHCO), 3.35 (3H, s, MeO), 2.45 (1H, dd, CH), 2.35 (1H, dd, CH), 2.10-2.05 (5H, m, CH2+CH3), 1.65 (3H, s, CH3). The epimer at the 4 position, 4(S)-Acetyl-5-[4-methoxy-3-(3-methoxy-propoxy)-phenyl]-pyrrolidine-2-carboxylic acid benzhydryl ester 1H-NMR, δ CDCl3: 7.40-7.25 (10H, m, Ph), 6.941 (1H, Brs, NH), 6.80 (3H, m, Ph), 4.68 (1H, d, NCHCO), 4.35 (1H, dd, PhCHN), 4.10-4.03 (3H, m, CH2O+CH), 3.85 (3H, s, MeO), 3.8 (2H, t, CH2C), 3.38-3.30 (4H, m, MeO+CHCO), 2.75 (2H, m, CH2), 2.08 (5H, m, CH2+CH3), 1.58 (3H, s, CH3), can also be isolated from this reaction.

Sources & evidence

ORD record
ord-0bf5ac3a671e4bbda43b7964829259cb
Source dataset
uspto-grants-2011_07
Patent number
US07973175B2

Reaction notes

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