Boc-gly-pro-OH → (S)-{2-[2-(2-bromo-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester

HRID 716526Notes

Reaction equation

HRID 716526 reaction equation
Cl.BrC1SC2=NC(N)=CN2C=1.C(OC(NCC(N1CCC[C@H]1C(O)=O)=O)=O)(C)(C)C.[C:31]([O:35][C:36](=[O:64])[NH:37][C@@H:38](C1C=CC=CC=1)[C:39]([N:41]1[CH2:45][CH2:44][CH2:43][C@H:42]1[C:46](=[O:57])[NH:47][C:48]1[N:49]=[C:50]2[N:54]([CH:55]=1)[CH:53]=[C:52]([Br:56])[S:51]2)=[O:40])([CH3:34])([CH3:33])[CH3:32]>>[C:31]([O:35][C:36](=[O:64])[NH:37][CH2:38][C:39]([N:41]1[CH2:45][CH2:44][CH2:43][C@H:42]1[C:46](=[O:57])[NH:47][C:48]1[N:49]=[C:50]2[N:54]([CH:55]=1)[CH:53]=[C:52]([Br:56])[S:51]2)=[O:40])([CH3:34])([CH3:32])[CH3:33]

Participants

4

Reactant 3

HCID 11673468Boc-gly-pro-OHHCID 672405282-Bromo-imidazo[2,1-b]thiazol-6-ylamine hydrochlorideHCID 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

Product 1

HCID 67239851(S)-{2-[2-(2-bromo-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl esterYield 46%

Procedure

Compound 28 was synthesized from compound 11 (0.471 mmol) and compound 27 (0.707 mmol), following the procedure as described for compound 23, as an off-white solid in 46% yield. MS (ESI, EI+) m/z=471.99-474.01 (MH+).

Sources & evidence

ORD record
ord-e104f9fa4ba543088edecc87b795062b
Source dataset
uspto-grants-2015_11
Patent number
US09187496B2

Reaction notes

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