Hydrochloric Acid → (5R,8S)-7-[(S)-2-Amino-2-(4-methyl-tetrahydro-pyran-4-yl)-acetyl]-10,10-di methyl-7-aza-dispiro-[3.0.4.1]decane-8-carboxylic acid [(1R,2S)-1-(pyrrolidine-1-sulfonylaminocarbonyl)-2-vinyl-cyclopropyl]-amide

HRID 1502201Notes

Reaction equation

HRID 1502201 reaction equation
C(OC(=O)[NH:7][C@@H:8]([C:42]1([CH3:48])[CH2:47][CH2:46][O:45][CH2:44][CH2:43]1)[C:9]([N:11]1[C@H:22]([C:23](=[O:41])[NH:24][C@:25]2([C:30]([NH:32][S:33]([N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)(=[O:35])=[O:34])=[O:31])[CH2:27][C@H:26]2[CH:28]=[CH2:29])[CH2:21][C@:13]2([C:18]([CH3:20])([CH3:19])[C:14]32[CH2:17][CH2:16][CH2:15]3)[CH2:12]1)=[O:10])(C)(C)C.Cl>O1CCOCC1>[N:36]1([S:33]([NH:32][C:30]([C@@:25]2([NH:24][C:23]([C@@H:22]3[CH2:21][C@:13]4([C:18]([CH3:20])([CH3:19])[C:14]54[CH2:15][CH2:16][CH2:17]5)[CH2:12][N:11]3[C:9](=[O:10])[C@@H:8]([NH2:7])[C:42]3([CH3:48])[CH2:43][CH2:44][O:45][CH2:46][CH2:47]3)=[O:41])[CH2:27][C@H:26]2[CH:28]=[CH2:29])=[O:31])(=[O:34])=[O:35])[CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59533207[(S)-2-{(5R,8S)-10,10-Dim ethyl-8-[(1R,2S)-1-(pyrrolidine-1-sulfonylaminocarbonyl)-2-vinyl-cyclopropyl-carbamoyl]-7-aza-dispiro[3.0.4.1]dec-7-yl}-1-(4-methyl-tetrahydro-pyran-4-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 59533255(5R,8S)-7-[(S)-2-Amino-2-(4-methyl-tetrahydro-pyran-4-yl)-acetyl]-10,10-di methyl-7-aza-dispiro-[3.0.4.1]decane-8-carboxylic acid [(1R,2S)-1-(pyrrolidine-1-sulfonylaminocarbonyl)-2-vinyl-cyclopropyl]-amide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of [(S)-2-{(5R,8S)-10,10-Dimethyl-8-[(1R,2S)-1-(pyrrolidine-1-sulfonylaminocarbonyl)-2-vinyl-cyclopropyl-carbamoyl]-7-aza-dispiro[3.0.4.1]dec-7-yl}-1-(4-methyl-tetrahydro-pyran-4-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (0.415 g; 0.588 mmol) and 13.0 mL HCl (4 M in dioxane) in 10 mL dioxane was stirred overnight at ambient temperature. The mixture was concentrated under reduced pressure to yield the title compound which was used in the next step without further purification. LC-MS (method E): Rt=1.45 min; M/z=606 [M+]; HPLC (method A3): Rt=4.01 min

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-70e93684e8ae4366a2c7ecbc3ba78027
Source dataset
uspto-grants-2015_12
Patent number
US09206232B2

Reaction notes

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