Hydrochloric Acid → N-((R)-2'-oxo-1,1',2',3-tetrahydrospiro[inden-2,3'-pyrrolo[2,3-b]pyridin]-5-yl)-2-((R)-5-oxo-3-phenyl-8,11-dioxa-1,4-diazaspiro[5.6]dodecan-4-yl)acetamide

HRID 1615783Notes

Reaction equation

HRID 1615783 reaction equation
[O:1]=[C:2]1[C:7]2([CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8]2)[N:6](C(OC(C)(C)C)=O)[CH2:5][C@@H:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:3]1[CH2:27][C:28](=[O:48])[NH:29][C:30]1[CH:31]=[C:32]2[C:45](=[CH:46][CH:47]=1)[CH2:44][C@:34]1([C:42]3[C:37](=[N:38][CH:39]=[CH:40][CH:41]=3)[NH:36][C:35]1=[O:43])[CH2:33]2.Cl>CO>[O:43]=[C:35]1[NH:36][C:37]2=[N:38][CH:39]=[CH:40][CH:41]=[C:42]2[C@:34]21[CH2:33][C:32]1[C:45](=[CH:46][CH:47]=[C:30]([NH:29][C:28](=[O:48])[CH2:27][N:3]3[C:2](=[O:1])[C:7]4([CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8]4)[NH:6][CH2:5][C@H:4]3[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:31]=1)[CH2:44]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 49842606(R)-tert-butyl 5-oxo-4-(2-oxo-2-((R)-2'-oxo-1,1',2',3-tetrahydrospiro[inden-2,3'-pyrrolo-[2,3-b]pyridin]-5-ylamino)ethyl)-3-phenyl-8,11-dioxa-1,4-diazaspiro[5.6]-dodecane-1-carboxylate

Product 1

HCID 49842495N-((R)-2'-oxo-1,1',2',3-tetrahydrospiro[inden-2,3'-pyrrolo[2,3-b]pyridin]-5-yl)-2-((R)-5-oxo-3-phenyl-8,11-dioxa-1,4-diazaspiro[5.6]dodecan-4-yl)acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

0.27 g (0.41 mmol) (R)-tert-butyl 5-oxo-4-(2-oxo-2-((R)-2′-oxo-1,1′,2′,3-tetrahydrospiro[inden-2,3′-pyrrolo-[2,3-b]pyridin]-5-ylamino)ethyl)-3-phenyl-8,11-dioxa-1,4-diazaspiro[5.6]-dodecane-1-carboxylate in 5 ml of methanol were combined with 10 ml of a 1.25 M methanolic hydrochloric acid and stirred for 3 h at 50° C. The reaction mixture was concentrated by rotary evaporation and neutralised with saturated NaHCO3 solution. The precipitate formed was suction filtered, washed with water and dried.

Workup

  1. concentrationThe reaction mixture was concentrated by rotary evaporation
  2. customThe precipitate formed
  3. filtrationfiltered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-5bd392d9cb7a4a70a22d22a32ff091c4
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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