Trifluoroacetic acid methylene chloride → (11S)-5-methyl-3-(10-oxo-1,9-diazatricyclo[11.6.1.014,19]eicosa-13(20),14(19),15,17-tetraen-11-ylcarbamoyl)hexanoic acid

HRID 965137Notes

Reaction equation

HRID 965137 reaction equation
C([O:5][C:6](=[O:37])[CH2:7][CH:8]([C:13](=[O:36])[NH:14][C@H:15]1[CH2:33][C:32]2=[CH:34][N:25]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=32)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][NH:17][C:16]1=[O:35])[CH2:9][CH:10]([CH3:12])[CH3:11])(C)(C)C.FC(F)(F)C(O)=O.C(Cl)Cl>>[CH3:11][CH:10]([CH3:12])[CH2:9][CH:8]([C:13](=[O:36])[NH:14][C@H:15]1[CH2:33][C:32]2=[CH:34][N:25]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=32)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][NH:17][C:16]1=[O:35])[CH2:7][C:6]([OH:37])=[O:5]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 67693565(11S)-5-methyl-3-(10-oxo-1,9-diazatricyclo-[11.6.1.014,19]eicosa-13(20),14(19),15,17-tetraen-11-ylcarbamoyl)hexanoic acid t-butyl ester

Product 1

HCID 54460498(11S)-5-methyl-3-(10-oxo-1,9-diazatricyclo[11.6.1.014,19]eicosa-13(20),14(19),15,17-tetraen-11-ylcarbamoyl)hexanoic acid

Procedure

The less polar stereoisomer of (11S)-5-methyl-3-(10-oxo-1,9-diazatricyclo[11.6.1.014,19 ]eicosa-13(20),14(19),15,17-tetraen-11-yl-carbamoyl)hexanoic acid t-butyl ester (300 mg) was covered with 5 mL of a 10% trifluoroacetic acid/methylene chloride solution and left to stir. After 2.5 hours, TLC indicated that the reaction was complete. All volatiles were removed under reduced pressure. The residue was taken up in CH2Cl2 (40 mL) and transferred to separatory funnel and washed consecutively with 0.5% HCl (40 mL) and brine (40 mL). The organic phase was dried (MgSO4), filtered and concentrated to provide the less polar stereoisomer of (11S)-5-methyl-3-(10-oxo-1,9-diazatricyclo[11.6.1.014,19 ]eicosa-13(20),14(19),15,17-tetraen-11-ylcarbamoyl)hexanoic acid.

Workup

  1. waitleft
  2. customAll volatiles were removed under reduced pressure
  3. customtransferred to separatory funnel
  4. washwashed consecutively with 0.5% HCl (40 mL) and brine (40 mL)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-33ae295023ac4d029b618adb710ed0a8
Source dataset
uspto-grants-1998_06
Patent number
US05773428

Reaction notes

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