Potassium Hydroxide → HCID 9916286, compound

HRID 1954301Notes

Reaction equation

C[O:2][C:3]([C:5]1[C:9]([O:10][CH3:11])=[C:8]([S:12]([O:15][C:16]2[C:21]([CH2:22][CH3:23])=[CH:20][C:19]([C:24]3[C:36]4[C:35]([CH3:37])=[C:34]([CH3:38])[S:33][C:32]=4[CH:31]=[C:30]4[C:25]=3[CH:26]=[CH:27][CH:28]=[CH:29]4)=[CH:18][C:17]=2[CH2:39][CH3:40])(=[O:14])=[O:13])[S:7][CH:6]=1)=[O:4].[OH-].[K+]>>[CH3:38][C:34]1[S:33][C:32]2[CH:31]=[C:30]3[C:25](=[C:24]([C:19]4[CH:18]=[C:17]([CH2:39][CH3:40])[C:16]([O:15][S:12]([C:8]5[S:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:9]=5[O:10][CH3:11])(=[O:13])=[O:14])=[C:21]([CH2:22][CH3:23])[CH:20]=4)[C:36]=2[C:35]=1[CH3:37])[CH:26]=[CH:27][CH:28]=[CH:29]3

Participants

Reactant 2

HCID 14797Potassium Hydroxide

HCID 54021354HCID 54021354, compound

Product 1

HCID 9916286HCID 9916286, compoundYield 66%

Procedure

The title compound was prepared according to the procedure in Example 10, step 2, using 5-[4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2, 6-diethyl-phenoxysulfonyl]-4-methoxy-thiophene-3-carboxylic acid methyl ester (0.608 g, 1.02 mmol) and 1N KOH (5.11 mL). Purification on 2% H3PO4 /MeOH treated Biotage KP-Sil eluting with a 25, 40 & 60% EtOAc/hexane step gradient to give 0.390 g (66%) of the title compound as a white solid, mp >230° C. 1H NMR (DMSO-d6) δ 1.09 (t, 6 H), 1.58 (s, 3 H), 2.41 (s, 3 H), 2.57-2.69 (m, 4 H), 4.01 (s, 3 H), 7.18 (s, 2 H), 7.35-7.41 (m, 2 H), 7.44-7.48 (m, 1 H), 7.96 (d, 1 H), 8.49 (s, 1 H), 8.74 (s, 1 H), 13.39 (s, 1 H). IR (KBr) 2950, 1700, 1540, 1360 and 860 cm-1. mass spectrum (-ESI) m/z 579 (M-H). Anal. Calcd. for C30H28O6S3 : C, 62.05; H, 4.86; N, 0.00. Found: C, 25 62.15; H, 5.09; N, 0.06.

Workup

customThe title compound was prepared
customPurification on 2% H3PO4 /MeOH treated Biotage KP-Sil
washeluting with a 25, 40 & 60% EtOAc/hexane step gradient

Sources & evidence

ORD record: ord-19c8ec647ba745549aa2406802977026
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06121271

Reaction notes

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