(S,S)-1-(2-tert-butoxycarbonylamino-2-phenyl-acetyl)-pyrrolidine-2-carboxylic acid → (S,S) {2-[2-(2-bromo-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidin-1-yl]-2-oxo-1-phenyl-ethyl}-carbamic acid tert-butyl ester

HRID 716521Notes

Reaction equation

HRID 716521 reaction equation
Cl.BrC1SC2=NC(N)=CN2C=1.C(OC(N[C@@H](C1C=CC=CC=1)C(N1CCC[C@H]1C(O)=O)=O)=O)(C)(C)C.[C:37]([O:41][C:42](=[O:70])[NH:43][C@@H:44]([C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)[C:45]([N:47]1[CH2:51][CH2:50][CH2:49][C@@H:48]1[C:52](=[O:63])[NH:53][C:54]1[N:55]=[C:56]2[N:60]([CH:61]=1)[CH:59]=[C:58]([Br:62])[S:57]2)=[O:46])([CH3:40])([CH3:39])[CH3:38]>>[C:37]([O:41][C:42](=[O:70])[NH:43][C@@H:44]([C:64]1[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=1)[C:45]([N:47]1[CH2:51][CH2:50][CH2:49][C@H:48]1[C:52](=[O:63])[NH:53][C:54]1[N:55]=[C:56]2[N:60]([CH:61]=1)[CH:59]=[C:58]([Br:62])[S:57]2)=[O:46])([CH3:40])([CH3:38])[CH3:39]

Participants

4

Reactant 3

HCID 58310477(S,S)-1-(2-tert-butoxycarbonylamino-2-phenyl-acetyl)-pyrrolidine-2-carboxylic acidHCID 672405282-Bromo-imidazo[2,1-b]thiazol-6-ylamine hydrochlorideHCID 86654641(S,R)-{2-[2-(2-bromo-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidin-1-yl]-2-oxo-1-phenyl-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 67241361(S,S) {2-[2-(2-bromo-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidin-1-yl]-2-oxo-1-phenyl-ethyl}-carbamic acid tert-butyl ester

Procedure

Compound 23 was synthesized from compound 11 (0.471 mmol) and compound 22 (0.707 mmol), following the procedure as described for compound 12a. The reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate before washing sequentially with Na2CO3, HCl (0.5N), and brine. The organic layers were dried, filtered, and concentrated under reduced pressure. The crude was purified by chromatography on a silica gel column to give compound 23 as a yellow solid in 45% yield. MS (ESI, EI+) m/z=548.07-550.02 (MH+).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washbefore washing sequentially with Na2CO3, HCl (0.5N), and brine
  4. customThe organic layers were dried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-ea3104767f5a4ae18fff1c1f99330582
Source dataset
uspto-grants-2015_11
Patent number
US09187496B2

Reaction notes

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