Methanol → HCID 69780590, compound

HRID 1279010Notes

Reaction equation

S(Cl)([Cl:3])=O.[ClH:5].Cl.[NH2:7][CH:8]([CH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19]([NH2:23])=[N:18][CH:17]=[CH:16]2)[C:9]([OH:11])=[O:10].[CH3:24]O>>[ClH:3].[ClH:5].[CH3:24][O:10][C:9](=[O:11])[CH:8]([NH2:7])[CH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19]([NH2:23])=[N:18][CH:17]=[CH:16]2

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 69781264HCID 69781264, compound

Product 1

HCID 69780590HCID 69780590, compound

Conditions

Temperature: 50 °C

Procedure

1.1 mL of thionyl chloride was added to a cooled solution (ice bath) of 65 mg of amino acid 1i in 4 mL of methanol. After stirring at 50° C. for 3 hours the mixture was concentrated under reduced pressure to give 66 mg of methyl ester 1j. The crude product was used without further purification. 1H-NMR 200 MHz (CD3OD) δ: 3.36-3.59 (2H, m), 3.81 (3H, s), 4.53 (1H, t, J=7 Hz), 7.23 (1H, d, J=7 Hz), 7.60 (1H, d, J=7 Hz), 7.73 (1H, dd, J=9 Hz and J=2 Hz), 7.87 (1H, d, J=2 Hz), 8.47 (1H, d, J=9 Hz).

Workup

concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record: ord-97ff226cb4b64ccf8358e6dd4a28cb03
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06444672B1

Reaction notes

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