Trifluoroacetic acid → HCID 86715382, compound

HRID 630638Notes

Reaction equation

HRID 630638 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([O:24][C@:25]([CH3:76])([CH2:74][I:75])[C:26](=[O:73])[C@H:27]([CH2:69][CH:70]([CH3:72])[CH3:71])[NH:28][C:29](=[O:68])[C@H:30]([CH2:61][C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)[NH:31][C:32](=[O:60])[C@H:33]([CH2:56][CH:57]([CH3:59])[CH3:58])[NH:34][C:35](=[O:55])[C@H:36]([CH2:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[NH:37][C:38](=[O:46])[CH2:39][N:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1)(=[O:23])[CH2:9][CH2:10][C:11]([O:13]CC1C=CC(OC)=CC=1)=[O:12]>C(Cl)Cl>[CH2:61]([C@@H:30]([C:29](=[O:68])[NH:28][C@@H:27]([CH2:69][CH:70]([CH3:72])[CH3:71])[C:26](=[O:73])[C@:25]([CH2:74][I:75])([CH3:76])[O:24][C:8](=[O:23])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])[NH:31][C:32](=[O:60])[C@H:33]([CH2:56][CH:57]([CH3:59])[CH3:58])[NH:34][C:35](=[O:55])[C@H:36]([CH2:47][CH2:48][C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)[NH:37][C:38](=[O:46])[CH2:39][N:40]1[CH2:41][CH2:42][O:43][CH2:44][CH2:45]1)[C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86715380HCID 86715380, compound

Product 1

HCID 86715382HCID 86715382, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Referring to FIG. 43, TFA (6 mL) was added dropwise to a solution of compound (4S,7S,10S,13S,15S)-10-benzyl-16-iodo-7,13-diisobutyl-15-methyl-1-morpholino-2,5,8,11,14-pentaoxo-4-phenethyl-3,6,9,12-tetraazahexadecan-15-yl 4-methoxybenzyl succinate (21, 1.7 g, 1.59 mmol) in DCM (30 mL) at 0° C. and the reaction mixture was allowed to warm to room temperature and stirred for 0.5 h. TFA was removed under reduced pressure and the residue was dissolved in DCM (50 mL). The resulting mixture was washed with water (40 mL×3) and brine (50 mL), dried over anhydrous Na2SO4 and concentrated to give product (quantitative without further purification).

Workup

  1. customTFA was removed under reduced pressure
  2. dissolutionthe residue was dissolved in DCM (50 mL)
  3. washThe resulting mixture was washed with water (40 mL×3) and brine (50 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto give
  7. customproduct (quantitative without further purification)

Sources & evidence

ORD record
ord-ac766eee70ba462e93cd139030d323e1
Source dataset
uspto-grants-2016_04
Patent number
US09315542B2

Reaction notes

Loading…