1-benzyl hydrogen (R)-pyrrolidine-1,2-dicarboxylate → HCID 68477807, compound

HRID 1807824Notes

Reaction equation

HRID 1807824 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:17]([N:27]1[CH2:34][CH2:33][CH2:32][C@@H:28]1[C:29](O)=[O:30])([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].C(OC1C=CC(NC(C2C=CC=CN=2)=O)=CC=1)C1C=CC=CC=1>>[CH2:20]([O:19][C:17]([N:27]1[CH2:34][CH2:33][CH2:32][C@@H:28]1[C:29](=[O:30])[NH:14][C:13]1[CH:12]=[CH:11][C:10]([O:9][CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[CH:16][CH:15]=1)=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 1112081-benzyl hydrogen (R)-pyrrolidine-1,2-dicarboxylateHCID 2425421N-[4-(benzyloxy)phenyl]pyridine-2-carboxamideHCID 27238314-Benzyloxyaniline hydrochloride

Product 1

HCID 68477807HCID 68477807, compound

Procedure

This compound was prepared from 4-benzyloxyaniline hydrochloride (4.0 g, 17.0 mmol) and (+)-N-carbobenzyloxy-d-proline (4.44 g, 17.8 mmol), using the same method to prepare pyridine-2-carboxylic acid (4-benzyloxyphenyl)amide, to give the product as a colorless solid, which was used without further purification in the subsequent step. 1H NMR (DMSO-d6) δ 1.80-1.95 (m, 3H), 2.10-2.27 (m, 1H), 3.35-3.55 (m, 2H), 4.33 (m, 1H), 5.0 (m, 4H), 6.95 (d, 2H), 7.12-7.53 (m, 12H) and 9.95 (d, 1H).

Sources & evidence

ORD record
ord-4a20c5859be9416c9972eada206ddd07
Source dataset
uspto-grants-2013_01
Patent number
US08357715B2

Reaction notes

Loading…