5-Methoxytryptophan → HCID 11510523, compound

HRID 2104208Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:17]=[C:16]2[C:6]([NH:7][CH:8]=[C:9]2[CH2:10][CH:11]([C:13]([OH:15])=[O:14])[NH2:12])=[CH:5][CH:4]=1.[CH2:18]([O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1)[C:19]#[C:20][CH3:21]>>[CH2:18]([O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:12][CH:11]([CH2:10][C:9]2[C:16]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:17]=3)[NH:7][CH:8]=2)[C:13]([OH:15])=[O:14])(=[O:31])=[O:30])=[CH:25][CH:24]=1)[C:19]#[C:20][CH3:21]

Participants

Reactant 2

HCID 1198025-Methoxytryptophan

HCID 111959284-But-2-ynyloxy-benzenesulfonyl chloride

Product 1

HCID 11510523HCID 11510523, compound

Procedure

The title compound was prepared by the method of Example 6, using 5-methoxy-DL-tryptophan and 4-but-2-ynyloxy-benzenesulfonyl chloride as starting materials. 1H NMR (DMSO-d6): 400 MHz δ 12.55 (bs, 1H), 10.63 (s, 1H), 8.06 (d, J=8.0 Hz, 1H), 7.53 (dd, J=8.0, 4.0 Hz, 2H), 7.18 (d, J=8.0 Hz, 1H), 7.02 (d, J=2.0 Hz, 1H), 6.92 (d, J=8.0 Hz, 2H), 6.82 (d, J=2.0 Hz, 1H), 6.68 (dd, J=8.0, 2.0 Hz, 1H), 4.78 (q, J=2.0 Hz, 2H), 3.87 (q, J=7.6 Hz, 1H), 3.72 (s, 3H), 3.00 (dd J=14.4, 6.4 Hz, 1H), 2.82 (dd J=14.4, 7.6 Hz, 1H), 1.83 (t, J=2.0 Hz, 3H); HRMS: calcd for C22H24N2O6S (ESI+, [M+H]1+), 443.1271; found 443.1265; LCMS m/z (ESI) [M+H] 443, retention time=2.50 min.

Sources & evidence

ORD record: ord-ffd8f311736c4883bd56ad7f98056bf5
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576222B2

Reaction notes

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