p-Toluenesulfonic acid monohydrate → HCID 86644640, compound

HRID 1662080Notes

Reaction equation

HRID 1662080 reaction equation
C(OC([NH:8][C@H:9]1[CH2:11][C@H:10]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=O)(C)(C)C.O.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26]([OH:29])(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(OCC)C>[C:20]1([CH3:30])[CH:21]=[CH:22][C:23]([S:26]([OH:29])(=[O:27])=[O:28])=[CH:24][CH:25]=1.[NH2:8][C@H:9]1[CH2:11][CH2:21][CH2:20][C@H:10]1[C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 67430396HCID 67430396, compound

Product 1

HCID 86644640HCID 86644640, compoundYield 180.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of tert-butyl rel-(1R,2S)-2-[(tert-butoxycarbonyl)amino]cyclopropanecarboxylate (0.54 g) and diethyl ether (4.0 ml) was added a solution of p-toluene sulfonic acid monohydrate (0.40 g) in diethyl ether (16 ml) at room temperature, followed by stirring at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure to obtain tert-butyl rel-(1R,2S)-2-aminocyclopentanecarboxylate p-toluene sulfonate (0.68 g). Tert-butyl rel-(1R,2S)-2-({N5-[(benzyloxy)carbonyl]-N2-[(1-methyl-1H-indol-2-yl)carbonyl]-L-ornithyl}amino)cyclopropanecarboxylate (0.20 g) was obtained by using tert-butyl rel-(1R,2S)-2-aminocyclopropanecarboxylate p-toluene sulfonate (0.64 g) in the same method as for Production Process A1.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2028c99311954e77940959b69f64a1b1
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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