tert-Butanol → 5-[(cyclopentylcarbonyl)amino]-2-[(2-naphthyloxy)methyl]-1-(4-oxo-4-{[(trifluoromethyl)sulfonyl]amino}butyl)-1H-indole-3-carboxylic Acid

HRID 895768Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

The product of Step 1, Example 53B (1 eq) was weighed into a flask along with NaH2PO4 (12 eq), t-butyl alcohol (0.12 M), water (0.12 M), 2-methyl-2-butene (50 eq) and to this mixture was added NaO2Cl (11.8 eq) at 25° C. Reaction mixture was then heated at 60° C., 3 h and left overnight at 25° C. Workup with ethyl acetate/water followed by chromatographic purification and triturations with CH2Cl2/hexane (1:1) afforded the desired product in 57% yield.

Workup

customReaction mixture
customWorkup with ethyl acetate/water followed by chromatographic purification and triturations with CH2Cl2/hexane (1:1)

Sources & evidence

ORD record: ord-d05a5ddd5839472ba7c5b1db03e72cd8
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06916841B2

Reaction notes

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