HCID 57447918, compound → HCID 87678770, compound

HRID 2101220Notes

Reaction equation

HRID 2101220 reaction equation
C(OC([NH:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][CH:16]([CH:24]([S:45]CC2C=CC(OC)=CC=2)[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([N:35]([CH3:44])[CH2:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:34])[CH:28]=2)[C:17]([O:19]C(C)(C)C)=[O:18])=[CH:11][CH:10]=1)=O)(C)(C)C>C([SiH](CC)CC)C.FC(F)(F)C(O)=O>[NH2:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][CH:16]([CH:24]([SH:45])[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([N:35]([CH3:44])[CH2:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:34])[CH:28]=2)[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 57447918HCID 57447918, compound

Product 1

HCID 87678770HCID 87678770, compoundYield 126.4%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 12052TriethylsilaneSolvent

Conditions

Temperature
60 °C

Procedure

tert-butyl 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-3-[(4-methoxybenzyl)thio]-5-(3-{[methyl(2-phenylethyl)amino]carbonyl}phenyl)pentanoate (80 mg, 0.106 mmol) was dissolved in triethylsilane (0.4 mL) and trifluoroacetic acid (3.0 mL). The solution was heated to 60° C. for 1 h and was then concentrated. Purification of the residue by reversed-phase HPLC (C-8 column, linear gradient 20%→100% of MeCN in 5% aqueous MeCN containing 0.15% trifluoroacetic acid) gave the title diastereomeric compound as the trifluoroacetic salt (64 mg, 100%) after freeze-drying.

Workup

  1. concentrationwas then concentrated
  2. customPurification of the residue by reversed-phase HPLC (C-8 column, linear gradient 20%→100% of MeCN in 5% aqueous MeCN containing 0.15% trifluoroacetic acid)

Sources & evidence

ORD record
ord-c6abc63547cf4de6b97e81cb12a3563e
Source dataset
uspto-grants-2009_08
Patent number
US07572817B2

Reaction notes

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