HCID 69076973, compound → HCID 10069101, compound

HRID 2101216Notes

Reaction equation

HRID 2101216 reaction equation
[C:1]1([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH:9]([S:33]CC2C=CC(OC)=CC=2)[CH:10]([CH2:18][C:19]2[CH:20]=[N:21][C:22]([NH:25]C(OC(C)(C)C)=O)=[CH:23][CH:24]=2)[C:11]([O:13]C(C)(C)C)=[O:12])[CH:2]=1>C([SiH](CC)CC)C.FC(F)(F)C(O)=O>[NH2:25][C:22]1[N:21]=[CH:20][C:19]([CH2:18][CH:10]([CH:9]([SH:33])[CH2:8][CH2:7][C:3]2[CH:2]=[C:1]([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[CH:6]=[CH:5][CH:4]=2)[C:11]([OH:13])=[O:12])=[CH:24][CH:23]=1

Participants

4

Reactant 1

HCID 69076973HCID 69076973, compound

Product 1

HCID 10069101HCID 10069101, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 12052TriethylsilaneSolvent

Conditions

Temperature
60 °C

Procedure

tert-Butyl 5-(1,1′-biphenyl-3-yl)-2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-3-[(4-methoxybenzyl)thio]pentanoate (0.669 g, 1.00 mmol) was dissolved in triethylsilane (0.75 mL) and trifluoroacetic acid (6.0 mL). The solution was heated to 60° C. for 3 h and then concentrated. Purification of the residue by reversed-phase HPLC (C-8 column, linear gradient 40%→100% of MeCN in 5% aqueous MeCN containing 0.15% trifluoroacetic acid) gave the title diastereomeric compound as the trifluoroacetic salt (0.342 g, 68%) after freeze-drying.

Workup

  1. concentrationconcentrated
  2. customPurification of the residue by reversed-phase HPLC (C-8 column, linear gradient 40%→100% of MeCN in 5% aqueous MeCN containing 0.15% trifluoroacetic acid)

Sources & evidence

ORD record
ord-2bb95a11996441a187383a8bfec5e09b
Source dataset
uspto-grants-2009_08
Patent number
US07572817B2

Reaction notes

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