methyl (S)-lactate → HCID 54052357, compound

HRID 1873173Notes

Reaction equation

[CH:1]1[C:9]2[C:8]3[C:10]([C:18]4[CH:23]=[C:22]([I:24])[C:21]([OH:25])=[C:20]([I:26])[CH:19]=4)=[C:11]4[C:16](=[CH:17][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1)[CH:15]=[CH:14][CH:13]=[CH:12]4.[C:27]([O:32]C)(=[O:31])[C@H:28]([CH3:30])O>>[CH:1]1[C:9]2[C:8]3[C:10]([C:18]4[CH:19]=[C:20]([I:26])[C:21]([O:25][C@H:28]([CH3:30])[C:27]([OH:32])=[O:31])=[C:22]([I:24])[CH:23]=4)=[C:11]4[C:16](=[CH:17][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1)[CH:15]=[CH:14][CH:13]=[CH:12]4

Participants

Reactant 2

HCID 94386methyl (S)-lactate

HCID 15481245HCID 15481245, compound

Product 1

HCID 54052357HCID 54052357, compound

Procedure

Prepared from of 4-(benzo[b]naphtho[2,3-d]thiophen-11-yl)-2,6-diiodo-phenol (Example 26) and commercially available (S)-lactic acid, methyl ester. White solid: mp 134-136: NMR (CDCl3): δ8.38 (s, 1 H), 7.95 (dd J=8, 6 Hz, 1 H), 7.93 (d, J=1 Hz, 2 H), 7.81 (d, J=8 Hz, 1 H), 7.58 (ddd, J=8, 7, 1 Hz, 1 H), 7.59-7.54 (m, 2 H), 7.49-7.40 (m, 2 H), 7.15(ddd, J=8, 7, 1 Hz, 1 H), 6.77 (d, J=8, 1 Hz, 1 H), 5.48 (q, J =7 Hz, 1 H), 1.82 (d, J=7 Hz, 2 H); MS (+FAB): [M+H]+, 651; Anal. Calc. for C26H16I2O3S: C, 46.18, H, 2.48, N, 0.00. Found: C, 46.60, H, 2.50, N, 0.21.

Sources & evidence

ORD record: ord-9ebf44f9f515456a9a0c36e0f4bcf0e6
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06110962

Reaction notes

Loading…