Trifluoroacetic acid → HCID 22884109, compound

HRID 1598463Notes

Reaction equation

HRID 1598463 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:25]=2[N:24]=[CH:23][CH:22]=[CH:21]3)=[O:15])[CH2:10][C@@H:9]1[CH2:26][CH2:27][O:28][CH2:29][CH2:30][CH3:31])=O)(C)(C)C.FC(F)(F)C(O)=O.FC(F)(F)C([O-])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:60]([O:64][C:65]([NH:67][C@@H:68]([CH2:71][S:72][C:73]([C:86]1[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=1)([C:80]1[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1)[C:74]1[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=1)[CH:69]=O)=[O:66])([CH3:63])([CH3:62])[CH3:61]>ClCCl.ClC(Cl)C>[C:60]([O:64][C:65]([NH:67][C@@H:68]([CH2:71][S:72][C:73]([C:74]1[CH:75]=[CH:76][CH:77]=[CH:78][CH:79]=1)([C:86]1[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=1)[C:80]1[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1)[CH2:69][N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:25]=2[N:24]=[CH:23][CH:22]=[CH:21]3)=[O:15])[CH2:10][C@@H:9]1[CH2:26][CH2:27][O:28][CH2:29][CH2:30][CH3:31])=[O:66])([CH3:63])([CH3:62])[CH3:61]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 84468TrifluoroacetateHCID 5049666Sodium triacetoxyborohydrideHCID 10388929N-Boc-S-trityl-(L)-cysteinalHCID 22884125HCID 22884125, compound

Product 1

HCID 22884109HCID 22884109, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

The product of Step B (0.330 g, 0.772 mmol) was first treated with trifluoroacetic acid (10 mL) in dichloromethane (10 mL); the crude trifluoroacetate salt was then reacted with sodium triacetoxyborohydride (0.653 g, 3.09 mmol), 2(R)-tert-butoxycarbonylamino-3-triphenylmethylthiopropanal (0.415 g, 0.927 mmol) in dichloroethane (15 mL) in the presence of crashed molecular sieves following the procedure described in Example 1, Step D. The title compound was obtained as a gum (0.572 g).

Sources & evidence

ORD record
ord-b5652c382adf404e94a25a00aef561ea
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

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