Benzyloxycarbonyl-L-proline → HCID 68480254, compound

HRID 1474504Notes

Reaction equation

HRID 1474504 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 101987Benzyloxycarbonyl-L-prolineHCID 2425421N-[4-(benzyloxy)phenyl]pyridine-2-carboxamideHCID 27238314-Benzyloxyaniline hydrochloride

Product 1

HCID 68480254HCID 68480254, compound

Procedure

This compound was prepared from 4-benzyloxyaniline hydrochloride (4.0 g, 17.0 mmol) and (−)-N-carbobenzyloxy-l-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, 7.51 g (98%), which was used without further purification in the subsequent step. MS m/z 431 (MH+). 1H NMR(CDCl3) δ 1.83-2.61 (m, 4H), 3.44-3.65 (m, 2H), 4.40-4.55 (m, 1H), 5.03 (s, 2H), 5.22 (br s, 2H), 6.90 (d, 2H) and 7.20-7.45 (m, 12H).

Sources & evidence

ORD record
ord-1f2d182b880b4eb59c156d6d9b796cab
Source dataset
uspto-grants-2015_04
Patent number
US09018241B2

Reaction notes

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