Water → HCID 69619745, compound

HRID 1737416Notes

Reaction equation

C1(C)C=CC(S(O[CH2:11][C@@H:12]2[O:25][C:16]3=[C:17]4[C:21](=[CH:22][CH:23]=[C:15]3[O:14][CH2:13]2)[NH:20][C:19](=[O:24])[CH2:18]4)(=O)=O)=CC=1.[C:27]1([CH2:33][CH2:34][CH2:35][CH2:36][NH2:37])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>CS(C)=O>[C:27]1([CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:12]2([CH3:11])[O:25][C:16]3=[C:17]4[C:21](=[CH:22][CH:23]=[C:15]3[O:14][CH2:13]2)[NH:20][C:19](=[O:24])[CH2:18]4)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 85 °C

Procedure

(R)-2-(Toluene-4-sulfonyloxymethyl)-2,3,8,9-tetrahydro-7H-1,4-dioxino[2,3-e]indol-8-one (1.05 g, 2.80 mmole) and phenylbutylamine (1.99 ml, 12.5 mmole) were combined in 15 ml of dry DMSO and heated to 85° C. for 4 hours under a nitrogen atmosphere. After cooling to room temperature, 200 ml of water was added and the mixture was extracted twice with 300 ml portions of 50% ethyl acetate in hexane. The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated in vacuum to yield an oil, which was column chromatographed on silica gel using 1% methanol/CH2Cl2 as eluant. The free base of the title compound (0.26 g, 30%) thus obtained was crystallized from ethanol with the addition of one equivalent of fumaric acid to give 0.25 g of the (S) enantiomer of the title compound as an tan solid fumarate, one-half hydrate, m.p. 185-186° C.

Workup

temperatureAfter cooling to room temperature
extractionthe mixture was extracted twice with 300 ml portions of 50% ethyl acetate in hexane
washThe combined organic phases were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuum
customto yield an oil, which
customchromatographed on silica gel using 1% methanol/CH2Cl2 as eluant

Sources & evidence

ORD record: ord-e09a1628860d443e933831b46d0ef0db
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05962465

Reaction notes

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