Efavirenz aminoalcohol → Efavirenz

HRID 1967182Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C@@:9]([OH:19])([C:14]#[C:15][CH:16]1[CH2:18][CH2:17]1)[C:10]([F:13])([F:12])[F:11].Cl[C:21]([O-])=[O:22]>>[CH:6]1[C:5]([Cl:8])=[CH:4][C:3]2[C@:9]([C:10]([F:13])([F:11])[F:12])([C:14]#[C:15][CH:16]3[CH2:18][CH2:17]3)[O:19][C:21]([NH:1][C:2]=2[CH:7]=1)=[O:22]

Participants

Reactant 2

HCID 11033574Efavirenz aminoalcohol

HCID 21226386Carbonochloridate2×

Product 1

HCID 64139Efavirenz

Procedure

This intermediate, (2S)-2-(2-amino-5-chlorophenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol, as a free base, is reacted with a chloroformate derivative in basic conditions to give, after 1 to 6 hours reaction, an alkyl carbamate intermediate (reaction of the amine moiety of intermediate (II) with the chloroformate derivative) that is then cyclized to yield Efavirenz.

Workup

customto give, after 1 to 6 hours
customreaction

Sources & evidence

ORD record: ord-df8a0f211d594f99964a4e657841d540
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420808B2

Reaction notes

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