Acetyl chloride → HCID 66930179, compound

HRID 218082Notes

Reaction equation

HRID 218082 reaction equation
C(O[C:6]([N:8]1[CH2:12][C@@H:11]([Cl:13])[C@H:10]2[O:14][CH2:15][C@@H:16]([OH:17])[C@H:9]12)=[O:7])(C)(C)C.C(Cl)(=O)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:46]([NH:53][C@H:54](C(O)=O)[CH2:55][CH:56]([CH3:58])[CH3:57])([O:48]C(C)(C)C)=O.Cl.[F:63][C:64]1[CH:65]=[C:66]([CH:70]=[CH:71][C:72]=1[C:73]1[N:74]=[C:75]([N:78]2[CH2:83][CH2:82][N:81]([CH3:84])[CH2:80][CH2:79]2)[S:76][CH:77]=1)C(O)=O>CO>[Cl:13][C@@H:11]1[CH2:12][N:8]([C:6]([C@@H:54]([NH:53][C:46](=[O:48])[C:66]2[CH:70]=[CH:71][C:72]([C:73]3[N:74]=[C:75]([N:78]4[CH2:79][CH2:80][N:81]([CH3:84])[CH2:82][CH2:83]4)[S:76][CH:77]=3)=[C:64]([F:63])[CH:65]=2)[CH2:55][CH:56]([CH3:57])[CH3:58])=[O:7])[C@H:9]2[C@H:16]([OH:17])[CH2:15][O:14][C@H:10]12

Participants

7

Reactant 5

HCID 6367Acetyl chlorideHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66921046HCID 66921046, compoundHCID 131728709HCID 131728709, compound

Product 1

HCID 66930179HCID 66930179, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This compound was prepared from N—[(S)-1-((3S,3aS,6R,6aS)-6-chloro-3-hydroxy-hexahydro-furo[3,2-b]pyrrole-4-carboxylic acid tert-butyl ester by a series of deprotection (acetyl chloride, MeOH) and HATU-mediated coupling steps with Boc-leucine initially, and finally 3-fluoro-4-[2-(4-methylpiperazin-1-yl)-thiazol-4-yl]benzoic acid HCl salt prepared as described in Example 9.

Sources & evidence

ORD record
ord-8bd700069e0d45c3b5de57795a5430a3
Source dataset
uspto-grants-2012_06
Patent number
US08198283B2

Reaction notes

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