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

HRID 1811686Notes

Reaction equation

HRID 1811686 reaction equation
C(OC(N[C@H](C1C=CC=CC=1)C(N1CCC[C@H]1C(O)=O)=O)=O)(C)(C)C.Cl.BrC1SC2=NC(N)=CN2C=1.[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])(C)(C)[CH3:38]>>[CH2:37]([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])[CH3:38]

Participants

4

Reactant 3

HCID 10089106(S,R)-1-(2-tert-butoxycarbonylamino-2-phenylacetyl)-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 67240827(S,R)-{2-[2-(2-bromo-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidin-1-yl]-2-oxo-1-phenylethyl}-carbamic acid ethyl ester

Procedure

Compound 44 was synthesized from compounds 43 (0.377 mmol) and 11 (0.565 mmol), following the procedure as described for compound 12a, at room temperature overnight, to give compound 44 as a yellow oil in 66% yield. 1H NMR (DMSO-d6, 400 MHz) δ (ppm) 1.10 (t, 3H), 1.80 (m, 2H), 1.95 (m, 2H), 3.10 (m, 1H), 3.81 (m, 1H), 3.99 (m, 2H), 4.40 (m, 1H), 5.42 (m, 1H), 7.31 (m, 5H), 7.50 (d, 1H), 7.81 (s, 1H), 8.16 (s, 1H), 10.61 (s, 1H); MS (ESI, EI+) m/z=520-522 (MH+).

Sources & evidence

ORD record
ord-048621d9cffc44edbc72aa625f835b52
Source dataset
uspto-grants-2013_01
Patent number
US08362068B2

Reaction notes

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