Methanol → 119993-55-4

HRID 731342Notes

Reaction equation

S(Cl)([Cl:3])=O.[NH2:5][C@H:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[C:11]([OH:13])=[O:12].[CH3:14]O>>[ClH:3].[NH2:5][C@H:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[C:11]([O:13][CH3:14])=[O:12]

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 73305Cispentacin

Product 1

HCID 14698814119993-55-4

Conditions

Temperature: 25 °C

Procedure

Thionyl chloride (2.64 mL, 36.22 mmol) was added slowly to anhydrous methanol (50 mL) at 0° C. under a nitrogen atmosphere. (1R,2S)-2-Amino-cyclopentanecarboxylic acid (4.0 g, 24.15 mmol) was added to above solution. The resulting mixture was allowed to warm to 25° C. and stirred for 5 h. The reaction mixture was concentrated in vacuo to afford the desired product, methyl (1R,2S)-2-aminocyclopentanecarboxylate hydrochloride (4.32 g, 24.15 mmol, quantitative), as a clear oil. The crude product was used directly in the next step. 1H NMR (400 MHz, CD3OD) δ: 1.72-2.05 (4H, m), 2.16 (2H, m), 3.13 (1H, m), 3.75 (3H, s), 3.77 (1H, m).

Workup

concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-6168e034bbfa44ad818ac855b3003170
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582626B2

Reaction notes

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