(S)-methyl 2-hydroxy-3-phenylpropanoate → HCID 21970370, compound

HRID 1873175Notes

Reaction equation

HRID 1873175 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[C:17]3[C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[S:20][C:16]=3[C:15]([S:25][C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:5]=[C:4]([Br:32])[C:3]=1[OH:33].O[C@@H:35]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:36]([O:38]C)=[O:37]>>[Br:32][C:4]1[CH:5]=[C:6]([C:8]2[C:17]3[C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[S:20][C:16]=3[C:15]([S:25][C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:7]=[C:2]([Br:1])[C:3]=1[O:33][C@H:35]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:36]([OH:38])=[O:37]

Participants

3

Reactant 2

HCID 5289077(S)-methyl 2-hydroxy-3-phenylpropanoateHCID 18687834HCID 18687834, compound

Product 1

HCID 21970370HCID 21970370, compound

Procedure

Prepared from of 2,6-dibromo-4-[6-(pyridin-4-ylsulfanyl)-benzo [b]naphtho[2,3-d]thiophen-11-yl]-phenol (Example 65) and (S)-2-hydroxy-3-phenylpropionic acid, methyl ester (Example 96). White solid: NMR (DMSO- d6); δ13.3 (broad singlet, 1 H), 8:45 (m, 2 H), 8.37 (d, J=8 Hz, 1 H), 7.99 (d, J=8 Hz, 1 H), 7.85 (dd, J=7, 2 Hz, 2 H), 7.77-7.74 (m, 1 H), 7.66-7.65 (m, 2 H), 7.50 (t, J 7 Hz, 1 H), 7.43-7.25 (m, 8H), 6.68 (d, J=8 Hz, 1 H), 5.35 (dd, J 8 ,2 Hz, 1 H), 3.43 (d, J=7 Hz, 2 H); MS [+FAB]: [(M+H)+], 739.9 (70%), 741.9 (100%), 743.9 (90%); MS High resolution (FAB)+ve, calc mass for C36H24Br2NO3S2 739.95644; measured mass 739.96224, mass deviation 5.80 mmu. Anal. Calc. for C36H23Br2NO3S2: C, 55.58, H, 3.11, N, 1.80. Found: C, 55.38, H, 3.37, N, 1.92.

Sources & evidence

ORD record
ord-86c56d0fee654a3c9b0afe934838a186
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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