Hydrochloric Acid → [(2s)-2-Methyl-3,4-dihydro-2h-chromen-6-yl]acetic acid hydrochloride

HRID 47663Notes

Reaction equation

FC(F)(F)C(=O)[CH2:4][C@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:15][C:16]([O:18]CC)=[O:17])[CH:11]=2)[O:6]1.[ClH:24]>>[ClH:24].[CH3:4][C@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:15][C:16]([OH:18])=[O:17])[CH:11]=2)[O:6]1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 70018658HCID 70018658, compound

Product 1

HCID 69895460[(2s)-2-Methyl-3,4-dihydro-2h-chromen-6-yl]acetic acid hydrochloride

Procedure

The crude trifluoroacteyl protected amine of Example 5 was heated in 6N HCl (200 mL) at 80-95° C. for 2 hours under argon. The reaction became a white suspension after it was cooled down to room temperature. The solid was collected by vacuum filtration and dried by suction (5.95 g, 56%): 1H NMR (DMSO-d6) δ1.63 (m, 1H), 2.00 (m, 1H), 2.70 (m, 2H), 3.00 (m, 1H), 3.11 (m, 1H), 4.20 (m, 1H), 6.70 (d, J=8.7 Hz, 1H), 6.95 (d, J=9.0 Hz, 1H), 6.96 (s, 1H), 8.25 (s, broad, 3H); CI-MS m/z 222 (M+H+).

Workup

filtrationThe solid was collected by vacuum filtration
customdried by suction (5.95 g, 56%)

Sources & evidence

ORD record: ord-9b4d0bf3037d458b8b6466834cf8974e
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06699860B2

Reaction notes

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