Hydrochloric Acid → (5R,8S)-7-{(S)-2-[(S)-2-Amino-2-(1-methyl-cyclohexyl)-acetylamino]-3,3-dimethyl-butyryl}-10,10-dimethyl-7-aza-dispiro[3.0.4.1]decane-8-carboxylic acid [(1R,2S)-1-(pyrrolidine-1-sulfonylaminocarbonyl)-2-vinyl-cyclopropyl]-amide

HRID 1893093Notes

Reaction equation

HRID 1893093 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:16](=[O:56])[NH:17][C@H:18]([C:23]([N:25]1[C@H:36]([C:37](=[O:55])[NH:38][C@:39]2([C:44]([NH:46][S:47]([N:50]3[CH2:54][CH2:53][CH2:52][CH2:51]3)(=[O:49])=[O:48])=[O:45])[CH2:41][C@H:40]2[CH:42]=[CH2:43])[CH2:35][C@:27]2([C:32]([CH3:34])([CH3:33])[C:28]32[CH2:31][CH2:30][CH2:29]3)[CH2:26]1)=[O:24])[C:19]([CH3:22])([CH3:21])[CH3:20])[C:9]1([CH3:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)(C)(C)C.Cl>O1CCOCC1>[N:50]1([S:47]([NH:46][C:44]([C@@:39]2([NH:38][C:37]([C@@H:36]3[CH2:35][C@:27]4([C:32]([CH3:33])([CH3:34])[C:28]54[CH2:31][CH2:30][CH2:29]5)[CH2:26][N:25]3[C:23](=[O:24])[C@@H:18]([NH:17][C:16](=[O:56])[C@@H:8]([NH2:7])[C:9]3([CH3:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]3)[C:19]([CH3:22])([CH3:21])[CH3:20])=[O:55])[CH2:41][C@H:40]2[CH:42]=[CH2:43])=[O:45])(=[O:49])=[O:48])[CH2:54][CH2:53][CH2:52][CH2:51]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59533192[(S)-((S)-1-{(5R,8S)-10,10-Dimethyl-8-[(1R,2S)-1-(pyrrolidine-1-sulfonylaminocarbonyl)-2-vinyl-cyclopropylcarbamoyl]-7-aza-dispiro[3.0.4.1]decane-7-carbonyl}-2,2-dimethyl-propylcarbamoyl)-(1-methyl-cyclohexyl)-methyl]-carbamic acid tert-butyl ester

Product 1

HCID 59533250(5R,8S)-7-{(S)-2-[(S)-2-Amino-2-(1-methyl-cyclohexyl)-acetylamino]-3,3-dimethyl-butyryl}-10,10-dimethyl-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)—((S)-1-{(5R,8S)-10,10-Dimethyl-8-[(1R,2S)-1-(pyrrolidine-1-sulfonylaminocarbonyl)-2-vinyl-cyclopropylcarbamoyl]-7-aza-dispiro[3.0.4.1]decane-7-carbonyl}-2,2-dimethyl-propylcarbamoyl)-(1-methyl-cyclohexyl)-methyl]-carbamic acid tert-butyl ester (0.219 g; 0.27 mmol) and 2.0 mL HCl (4 M in dioxane) in 2 mL dioxane was stirred at ambient temperature for 2 h. The mixture was concentrated under reduced pressure and co-evaporated 2 times with DCM to yield the title compound which was used in the next step without further purification. LC-MS (method E): Rt=1.64 min; M/z=717 [M+]; HPLC (method A3): Rt=4.82 min

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1c59e1b1ba2f41798475c23bce0ec9f0
Source dataset
uspto-grants-2013_08
Patent number
US08512690B2

Reaction notes

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