(S)-methyl 2-hydroxy-3-phenylpropanoate → HCID 53790541, compound

HRID 1873165Notes

Reaction equation

HRID 1873165 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:14]([C:15]([C:25]#[N:26])=[C:16]4[S:20][C:19]5[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=5[C:17]=24)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:4][CH:3]=1.O[C@@H:28]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:29]([O:31]C)=[O:30]>C(Cl)(Cl)Cl>[C:25]([C:15]1[C:16]2[S:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[C:17]=2[C:8]([C:5]2[CH:4]=[CH:3][C:2]([O:1][C@H:28]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:29]([OH:31])=[O:30])=[CH:7][CH:6]=2)=[C:9]2[C:14]=1[CH:13]=[CH:12][CH:11]=[CH:10]2)#[N:26]

Participants

4

Reactant 2

HCID 5289077(S)-methyl 2-hydroxy-3-phenylpropanoateHCID 15481261HCID 15481261, compound

Product 1

HCID 53790541HCID 53790541, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Prepared from 11-(4-hydroxy-phenyl)-benzo [b]naphtho[2,3-d]thiophene-6-carbonitrile (Example 44) and (S)-2-hydroxy-3-phenylpropionic acid, methyl ester (Example 96). White solid: mp 145-148° C.: [a]D25=-2.03° (7.883 mg/mL CHCl3); NMR (CDCl3); δ8.31 (ddd, J=8, 1, 1 Hz, 1 H), 7.78 (ddd., J=8, 1, 1 Hz, 1 H), 7.70 (ddd, J=8, 8, 1 Hz, 1 H), 7.56 (ddd, J=8, 1, 1 Hz, 1 H), 7.47-7.37 (m, 6 H), 7.32 (ddd, J=8, 7, 1 Hz, 1 H), 7.20 (dd., J=8, 2 Hz, 1 H),7.14-7.05 (m, 4 H), 6.62 (ddd, J=8, 1, 1 Hz, 1 H), 5.06 (dd, J=7, 5 Hz, 1 H), 3.44 (d, J=5 Hz, 1 H), 3.42 (d, J=7 Hz, 1 H); MS (EI): [M+], 499 (100%); Anal. Calc. for C32H21NO3S: C, 76.93, H, 4.24, N, 2.80. Found: C, 75.77, H, 4.22, N, 2.70.

Sources & evidence

ORD record
ord-0ccc612ef7a847bc9db271598302ff36
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

Loading…