Hydrochloric Acid → HCID 178501194, compound

HRID 1694459Notes

Reaction equation

C[O:2][C:3]([C:5]1[S:6][C:7]([C:30]2[CH2:35][CH2:34][C:33]([CH3:37])([CH3:36])[CH2:32][CH:31]=2)=[CH:8][C:9]=1[N:10]([C@H:20]1[CH2:25][CH2:24][C@H:23]([O:26][CH2:27][O:28][CH3:29])[CH2:22][CH2:21]1)[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4].O.O[Li].O.Cl>C1COCC1.C(Cl)Cl.CO>[CH3:37][C:33]1([CH3:36])[CH2:34][CH2:35][C:30]([C:7]2[S:6][C:5]([C:3]([OH:4])=[O:2])=[C:9]([N:10]([C@H:20]3[CH2:25][CH2:24][C@H:23]([O:26][CH2:27][O:28][CH3:29])[CH2:22][CH2:21]3)[C:11]([C@H:13]3[CH2:14][CH2:15][C@H:16]([CH3:19])[CH2:17][CH2:18]3)=[O:12])[CH:8]=2)=[CH:31][CH2:32]1

Participants

Conditions

Temperature: 120 °C

Procedure

The methyl ester from Step I (285 mg, 0.54 mmol) was dissolved in a 4:2:1 mixture of THF:H2O:methanol (7 mL), LiOH.H2O (225 mg, 5.36 mmol) was added to solution, and it was heated in a microwave oven at 120° C. for 5 min, then for an additional 5 min at 130° C. The reaction mixture was diluted with CH2Cl2, acidified with 2N HCl, washed with brine, and organic fraction was dried over Na2SO4 and evaporated to dryness. The residue was purified by column chromatography on silicagel eluting with 0-10% MeOH in CH2Cl2 to give 265 mg (95%) of 5-(4,4-dimethyl-cyclohex-1-enyl)-3-[(trans-4-methoxymethoxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid.

Workup

washwashed with brine, and organic fraction
dry with materialwas dried over Na2SO4
customevaporated to dryness
customThe residue was purified by column chromatography on silicagel
washeluting with 0-10% MeOH in CH2Cl2

Sources & evidence

ORD record: ord-7900cf0865f3428f91cd77c2238e0392
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158675B2

Reaction notes

Loading…