Hydrochloric Acid → N-(3-{4-[(2S,3R)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-2-(4-hydroxyphenyl)-4-oxoazetidin-1-yl]phenyl}prop-2-yn-1-yl)methanesulfonamide

HRID 1437814Notes

Reaction equation

HRID 1437814 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]2[C@@H:18]([CH2:19][CH2:20][C@@H:21]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[OH:22])[C:17](=[O:30])[N:16]2[C:31]2[CH:36]=[CH:35][C:34]([C:37]#[C:38][CH2:39][NH:40][S:41]([CH3:44])(=[O:43])=[O:42])=[CH:33][CH:32]=2)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.Cl>C1COCC1>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C@@H:21]([OH:22])[CH2:20][CH2:19][C@H:18]2[C:17](=[O:30])[N:16]([C:31]3[CH:36]=[CH:35][C:34]([C:37]#[C:38][CH2:39][NH:40][S:41]([CH3:44])(=[O:43])=[O:42])=[CH:33][CH:32]=3)[C@@H:15]2[C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68975379N-[3-(4-{(2S,3R)-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-1-yl}phenyl)prop-2-yn-1-yl]methanesulfonamide

Product 1

HCID 67055618N-(3-{4-[(2S,3R)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-2-(4-hydroxyphenyl)-4-oxoazetidin-1-yl]phenyl}prop-2-yn-1-yl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10 mg of N-[3-(4-{(2S,3R)-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-1-yl}phenyl)prop-2-yn-1-yl]methanesulfonamide in 0.5 mL THF was added 0.5 mL of 2N aq. HCl. The resulting mixture was stirred at room temperature for 1 hr at which time the volatiles were removed under vacuum. The residue was purified by prep. Tlc eluting with CH2Cl2/MeOH (9/1) followed by further purification by prep. Tlc eluting with CH2Cl2/MeOH (95/5) afforded the title compound. m/z (ES) 544.9 (M+Na+), 523 (MH+), 505 (M−H2O+).

Workup

  1. customwere removed under vacuum
  2. customThe residue was purified by prep
  3. customTlc eluting with CH2Cl2/MeOH (9/1) followed by further purification by prep

Sources & evidence

ORD record
ord-581477fd0cfe4fb0b89011df28e5ef51
Source dataset
uspto-grants-2009_11
Patent number
US07622449B2

Reaction notes

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