(3R,4S)-3-Amino-1-[(7-chloro-1,2,3,4-tetrahydroisoquinolin-3-yl)carbonyl]-4-[3-(dihydroxyboryl)propyl]pyrrolidine-3-carboxylic acid dihydrochloride → HCID 57331597, compound

HRID 61405Notes

Reaction equation

HRID 61405 reaction equation
Cl.Cl.[NH2:3][C@:4]1([C:28]([OH:30])=[O:29])[C@@H:8]([CH2:9][CH2:10][CH2:11][B:12]([OH:14])[OH:13])[CH2:7][N:6]([C:15]([CH:17]2[CH2:26][C:25]3[C:20](=[CH:21][C:22]([Cl:27])=[CH:23][CH:24]=3)[CH2:19][NH:18]2)=[O:16])[CH2:5]1.N([C@]1(C(OCC(=O)C2C=CC=CC=2)=O)[C@@H](CCCB2OC(C)(C)C(C)(C)O2)CN(C(C2CC3C(=CC(Cl)=CC=3)CN2C(OC(C)(C)C)=O)=O)C1)=[N+]=[N-]>>[NH2:3][C@:4]1([C:28]([OH:30])=[O:29])[C@@H:8]([CH2:9][CH2:10][CH2:11][B:12]([OH:14])[OH:13])[CH2:7][N:6]([C:15]([CH:17]2[CH2:26][C:25]3[C:20](=[CH:21][C:22]([Cl:27])=[CH:23][CH:24]=3)[CH2:19][NH:18]2)=[O:16])[CH2:5]1

Participants

3

Reactant 2

HCID 67516455(3R,4S)-3-Amino-1-[(7-chloro-1,2,3,4-tetrahydroisoquinolin-3-yl)carbonyl]-4-[3-(dihydroxyboryl)propyl]pyrrolidine-3-carboxylic acid dihydrochlorideHCID 123350121HCID 123350121, compound

Product 1

HCID 57331597HCID 57331597, compound

Procedure

(3R,4S)-3-Amino-1-[(7-chloro-1,2,3,4-tetrahydroisoquinolin-3-yl)carbonyl]-4-[3-(dihydroxyboryl)propyl]pyrrolidine-3-carboxylic acid dihydrochloride (mixture of two diastereomers; each a racemate) is prepared in a manner analogous to that set forth in Example 54, Steps 2-3, except tert-butyl 3-({(3R,4S)-3-azido-3-[(2-oxo-2-phenylethoxy)carbonyl]-4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]pyrrolidin-1-yl}carbonyl)-7-chloro-3,4-dihydroisoquinoline-2(1H)-carboxylate (Step 2) is used as the substrate.

Sources & evidence

ORD record
ord-f830b3fbacae403d8c52d69da53d7993
Source dataset
uspto-grants-2016_09
Patent number
US09440995B2

Reaction notes

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