Acetonitrile → HCID 131732462, compound

HRID 1852376Notes

Reaction equation

HRID 1852376 reaction equation
[NH:1]([C:60]([O:62][CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)=[O:61])[C@H:2]([C:27]([N:29]1[CH2:59][CH2:58][CH2:57][C@H:30]1[C:31]([NH:33][C@H:34]([C:42]([NH:44][C@H:45]([C:54]([OH:56])=[O:55])[CH2:46][CH2:47][CH2:48][CH2:49][NH:50][C:51]([CH3:53])=[O:52])=[O:43])[CH2:35][CH2:36][CH2:37][CH2:38][N:39]([CH3:41])[CH3:40])=[O:32])=[O:28])[CH2:3][CH2:4][C:5](=[O:26])[NH:6]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[NH2:70][C:71]1[C:76]2[N:77]=[C:78]([C:80]#[N:81])[S:79][C:75]=2[CH:74]=[CH:73][CH:72]=1.C([SiH](C(C)C)C(C)C)(C)C.C(#N)C.C(O)(C(F)(F)F)=O>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH:1]([C:60]([O:62][CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)=[O:61])[C@H:2]([C:27]([N:29]1[CH2:59][CH2:58][CH2:57][C@H:30]1[C:31]([NH:33][C@H:34]([C:42]([NH:44][C@H:45]([C:54]([OH:56])=[O:55])[CH2:46][CH2:47][CH2:48][CH2:49][NH:50][C:51]([CH3:53])=[O:52])=[O:43])[CH2:35][CH2:36][CH2:37][CH2:38][N:39]([CH3:40])[CH3:41])=[O:32])=[O:28])[CH2:3][CH2:4][C:5](=[O:26])[NH2:6].[NH2:70][C:71]1[C:76]2[N:77]=[C:78]([C:80]#[N:81])[S:79][C:75]=2[CH:74]=[CH:73][CH:72]=1

Participants

6

Reactant 4

HCID 6342Acetonitrile2×HCID 6422Trifluoroacetic acidHCID 138754Silane, tris(1-methylethyl)-HCID 131732464HCID 131732464, compound

Product 1

HCID 131732462HCID 131732462, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of Cbz-Gln(Trt)ProLys(Me2)Lys(Ac)-aminocyanobenzothiazole (SEQ ID NO:3) (5.26) and triisopropylsilane (4 mL) in TFA/DCM (40 mL, 1/1) was stirred under a N2 atmosphere at −20° C. for 1 hour. After the conversion of starting material to a new species was confirmed by reverse phase HPLC (Agilent 1100 HPLC; column: Phenomonex Synergi, 4 μm 80 Å, 250×4.6 mm. method: 20% ACN to 55% ACN over 15 minutes, 1 mL/min, aqueous buffer contains 0.1% TFA v/v), the reaction mixture was concentrated. The resulting viscous sludge was then flooded with diethyl ether (200 mL), agitated for 5 minutes, and the solids collected via centrifugation and dried under full vacuum to provide crude Cbz-GlnProLys(Me2)Lys(Ac)-aminocyanobenzothiazole (SEQ ID NO:4) (4.4 g).

Workup

  1. concentrationwas concentrated
  2. customthe solids collected via centrifugation
  3. customdried under full vacuum

Sources & evidence

ORD record
ord-1887dc6980cf448eb822084c227df989
Source dataset
uspto-grants-2015_02
Patent number
US08962266B2

Reaction notes

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