2-(R)-Benzyloxycarbonylamino-3-(4-tert-butoxycarbonylamino-2-hydroxymethyl-3-methyl-phenyl)-propionic acid methyl ester hydrochloride → 2-(R)-Benzyloxycarbonylamino-3-(4-chloromethyl-1H-indazol-5-yl)-propionic acid methyl ester hydrochloride

HRID 132291Notes

Reaction equation

HRID 132291 reaction equation
Cl.COC(=O)[C@H]([NH:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])CC1C=CC(NC(OC(C)(C)C)=O)=C(C)C=1CO.Cl.[CH3:37][O:38][C:39](=[O:58])[C@@H:40]([CH2:46][C:47]1[C:48]([CH2:56][Cl:57])=[C:49]2[C:53](=[CH:54][CH:55]=1)[NH:52][N:51]=[CH:50]2)CC(OC)=O>>[ClH:57].[CH3:37][O:38][C:39](=[O:58])[C@H:40]([NH:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[CH2:46][C:47]1[C:48]([CH2:56][Cl:57])=[C:49]2[C:53](=[CH:54][CH:55]=1)[NH:52][N:51]=[CH:50]2

Participants

3

Reactant 2

HCID 673169532-(R)-Benzyloxycarbonylamino-3-(4-tert-butoxycarbonylamino-2-hydroxymethyl-3-methyl-phenyl)-propionic acid methyl ester hydrochlorideHCID 673178982-(S)-(4-Chloromethyl-1H-indazol-5-ylmethyl)-succinic acid dimethyl ester hydrochoride

Product 1

HCID 673183742-(R)-Benzyloxycarbonylamino-3-(4-chloromethyl-1H-indazol-5-yl)-propionic acid methyl ester hydrochlorideYield 99%

Procedure

2-(R)-Benzyloxycarbonylamino-3-(4-tert-butoxycarbonylamino-2-hydroxymethyl-3-methyl-phenyl)-propionic acid methyl ester hydrochloride was reacted in a manner analogous to the preparation of 2-(S)-(4-chloromethyl-1H-indazol-5-ylmethyl)-succinic acid dimethyl ester hydrochloride. Title compound was obtained as an orange solid in 99% yield. 1H NMR (300 MHz, CD3OD): δ=8.43 (s, 1H), 7.50 (d, J=8.8, 1H), 7.38 (d, J=8.4, 1H), 7.24 (m, 5H), 5.06 (d, J=1.0, 1H), 4.98 (d, J=4.8, 2H), 4.56 (dd, J1=5.7, J2=9.3, 1H), 3.71 (s, 3H), 3.42 (dd, J1=5.5, J2=14.3, 1H), 3.17 (dd, J1=9.3, J2=14.1, 1H). MS m/e (M+H)+=402.0.

Sources & evidence

ORD record
ord-08e0adb777ab4163a3f9ef30786b08c8
Source dataset
uspto-grants-2008_06
Patent number
US07384931B2

Reaction notes

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