Triethylamine → Methanesulfonic acid 2-{5-[3-phenyl-3-(3-trifluoromethyl-benzenesulfonylamino)-propionylamino]-5,6,7,8-tetrahydro-naphthalen-2-yl}-allyl Ester

HRID 32107Notes

Reaction equation

[OH:1][CH2:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]([NH:15][C:16](=[O:39])[CH2:17][CH:18]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[NH:19][S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=1)(=[O:22])=[O:21])[CH2:10][CH2:9][CH2:8]2)=[CH2:4].CCN(CC)CC.[CH3:47][S:48](Cl)(=[O:50])=[O:49]>C(Cl)Cl>[C:33]1([CH:18]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:31])[F:32])[CH:24]=2)(=[O:22])=[O:21])[CH2:17][C:16]([NH:15][CH:11]2[CH2:10][CH2:9][CH2:8][C:7]3[CH:6]=[C:5]([C:3](=[CH2:4])[CH2:2][O:1][S:48]([CH3:47])(=[O:50])=[O:49])[CH:14]=[CH:13][C:12]2=3)=[O:39])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a flask charged with N-[6-(1-hydroxymethyl-vinyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-3-phenyl-3-(3-trifluoromethyl-benzenesulfonylamino)-propionamide (Step F, 558 mg, 1.0 mmol, 1.0 eq) was added CH2Cl2 (7 mL) and Et3N (0.18 mL, 1.3 mmol, 1.3 eq). The suspension was cooled to 0° C., purged with N2, and then added the CH2Cl2 solution (1 mL) of methanesulfonyl chloride (Aldrich, 0.1 mL, 1.3 mmol, 1.3 eq). The mixture was concentrated in vacuo after 1 h. The crude was dried on vacuum and used for next step directly.

Workup

custompurged with N2
concentrationThe mixture was concentrated in vacuo after 1 h
customThe crude was dried on vacuum

Sources & evidence

ORD record: ord-97ded83fb07944e19cf0fbd49b64ea67
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425631B2

Reaction notes

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