Trifluoroacetic acid → HCID 21957075, compound

HRID 902944Notes

Reaction equation

HRID 902944 reaction equation
C([O:5][C:6](=[O:51])[CH:7]([NH:16][C:17](=[O:50])[CH:18]([CH2:42][C:43]([O:45]C(C)(C)C)=[O:44])[CH2:19][CH2:20][CH2:21][S:22]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:8][C:9]([O:11]C(C)(C)C)=[O:10])(C)(C)C.C(O)(C(F)(F)F)=O.C(S)(S)C.C([SiH](C(C)C)C(C)C)(C)C>C(Cl)Cl>[C:43]([CH2:42][CH:18]([CH2:19][CH2:20][CH2:21][SH:22])[C:17]([NH:16][CH:7]([CH2:8][C:9]([OH:11])=[O:10])[C:6]([OH:51])=[O:5])=[O:50])([OH:45])=[O:44]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 336451,1-EthanedithiolHCID 138754Silane, tris(1-methylethyl)-HCID 69211675HCID 69211675, compound

Product 1

HCID 21957075HCID 21957075, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the protected thiolate of Example 119 in CH2Cl2 (1 mL) was added at 0° C. a solution of 60% TFA in CH2Cl2, containing 2% of ethanedithiol. Triisopropyl silane (1%) was then added and the reaction mixture was stirred at room temperature for 1 hour after which it was first concentrated using a stream of argon and then under vacuum. The obtained white solid was washed several times with a mixture of diethyl ether/hexanes (3:1). The obtained white solid was purified by semi-preparative HPLC to provide the desired compound.

Workup

  1. concentrationwas first concentrated
  2. washThe obtained white solid was washed several times
  3. additionwith a mixture of diethyl ether/hexanes (3:1)
  4. customThe obtained white solid was purified by semi-preparative HPLC

Sources & evidence

ORD record
ord-f771b3dc56fa403d87e411331e2dae83
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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