Triethylsilane → (S)-2-{[(1R,2R,4S)-2-{(S)-1-[((S)-Cyclohexyl-methoxycarbonyl-methyl)-carbamoyl]-2-methyl-propylcarbamoyl}-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino}-pentanoic acid

HRID 2242441Notes

Reaction equation

HRID 2242441 reaction equation
C([O:5][C:6](=[O:59])[C@@H:7]([NH:11][C:12]([C@@H:14]1[CH2:18][C@@H:17]([O:19][C:20]2[C:29]3[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=3)[N:23]=[C:22]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:21]=2)[CH2:16][C@H:15]1[C:38](=[O:58])[NH:39][C@H:40]([C:44](=[O:57])[NH:45][C@@H:46]([CH:51]1[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]1)[C:47]([O:49][CH3:50])=[O:48])[CH:41]([CH3:43])[CH3:42])=[O:13])[CH2:8][CH2:9][CH3:10])(C)(C)C.C([SiH](CC)CC)C>C(Cl)Cl.FC(F)(F)C(O)=O>[CH:51]1([C@H:46]([NH:45][C:44]([C@@H:40]([NH:39][C:38]([C@@H:15]2[CH2:16][C@H:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:21]=3)[CH2:18][C@H:14]2[C:12]([NH:11][C@@H:7]([CH2:8][CH2:9][CH3:10])[C:6]([OH:59])=[O:5])=[O:13])=[O:58])[CH:41]([CH3:42])[CH3:43])=[O:57])[C:47]([O:49][CH3:50])=[O:48])[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 11274400(S)-2-{[(1R,2R,4S)-2-{(S)-1-[((S)-Cyclohexyl-methoxycarbonyl-methyl)-carbamoyl]-2-methyl-propylcarbamoyl}-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino}-pentanoic acid tert-butyl ester

Product 1

HCID 11468353(S)-2-{[(1R,2R,4S)-2-{(S)-1-[((S)-Cyclohexyl-methoxycarbonyl-methyl)-carbamoyl]-2-methyl-propylcarbamoyl}-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino}-pentanoic acidYield 100.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Tert.butyl ester 56 (28 mg, 0.034 mmol) and triethylsilane (14 μL, 0.088 mmol) was dissolved in DCM (2 mL) after which trifluoroacetic acid (2 mL) was added and the mixture was stirred for 2 h. Co-evaporation with toluene gave 57 (26 mg, 100%) as a colorless solid.

Workup

  1. additionwas added
  2. customCo-evaporation with toluene

Sources & evidence

ORD record
ord-dc270391820c4bcf9141234a40e92485
Source dataset
uspto-grants-2010_03
Patent number
US07671032B2

Reaction notes

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