Water → HCID 66859607, compound

HRID 1894845Notes

Reaction equation

[OH-].[Na+].C[O:4][C:5]([C:7]1[S:8][C:9]([C:45]#[C:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[CH:10][C:11]=1[N:12]([C:36]([CH:38]1[CH2:43][CH2:42][CH:41]([CH3:44])[CH2:40][CH2:39]1)=[O:37])[CH:13]1[CH2:18][CH2:17][C:16]([O:26][C:27]([CH:29]2[CH2:34][CH2:33][CH:32]([CH3:35])[CH2:31][CH2:30]2)=[O:28])([CH2:19][O:20][CH:21]2[CH2:25][CH2:24][O:23][CH2:22]2)[CH2:15][CH2:14]1)=[O:6].C1COCC1.O>CO>[CH3:49][C:47]([CH3:48])([CH3:50])[C:46]#[C:45][C:9]1[S:8][C:7]([C:5]([OH:6])=[O:4])=[C:11]([N:12]([C:36]([CH:38]2[CH2:39][CH2:40][CH:41]([CH3:44])[CH2:42][CH2:43]2)=[O:37])[CH:13]2[CH2:14][CH2:15][C:16]([O:26][C:27]([CH:29]3[CH2:34][CH2:33][CH:32]([CH3:35])[CH2:31][CH2:30]3)=[O:28])([CH2:19][O:20][CH:21]3[CH2:25][CH2:24][O:23][CH2:22]3)[CH2:17][CH2:18]2)[CH:10]=1

Participants

Conditions

Temperature: 70 °C

Procedure

NaOH (1.17 mL of a 1.0N aqueous solution) was added dropwise to a solution of 5-(3,3-dimethyl-but-1-ynyl)-3-{(4-methyl-cyclohexanecarbonyl)-[4-(4-methyl-cyclohexanecarbonyloxy)-4-(tetrahydro-furan-3-yloxymethy)-cyclohexyl]-amino}-thiophene-2-carboxylic acid methyl ester (80 mg, 0.117 mmol) in methanol (2 mL)/THF (2 mL)/H2O (2 mL) at room temperature. The solution was heated at 70° C. overnight and then cooled to room temperature. Volatiles were removed under vacuum and the resulting residue purified by HPLC with CH3CN (0.1% TFA)/H2O (0.1% TFA) to provide the Compound 4 (23.3 mg, 36%) as colorless solid. MS (m/z): 546.0[M+H]+; HPLC retention time 4.169 min (2-98% acetonitrile: water with 0.05% trifluoroacetic acid).

Workup

temperaturecooled to room temperature
customVolatiles were removed under vacuum
customthe resulting residue purified by HPLC with CH3CN (0.1% TFA)/H2O (0.1% TFA)

Sources & evidence

ORD record: ord-44327deaeba04443ba7d7215723e29d9
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513298B2

Reaction notes

Loading…