Hydrochloric Acid → Hydrochloric Acid

HRID 253601Notes

Reaction equation

HRID 253601 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:20][C:21]2[C:24](=[O:25])[C:23](=[O:26])[C:22]=2[N:27]2[CH2:32][CH2:31][CH2:30][CH:29]([CH:33]([O:40][CH2:41][CH2:42][CH2:43][O:44][CH3:45])[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:28]2)[C@H:9]([OH:19])[CH2:10][NH:11]C(=O)OC(C)(C)C)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:46]>O1CCOCC1>[NH2:11][CH2:10][C@@H:9]([OH:19])[C@@H:8]([NH:20][C:21]1[C:24](=[O:25])[C:23](=[O:26])[C:22]=1[N:27]1[CH2:32][CH2:31][CH2:30][CH:29]([CH:33]([O:40][CH2:41][CH2:42][CH2:43][O:44][CH3:45])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:28]1)[CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1.[ClH:46]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86761256HCID 86761256, compound

Product 2

HCID 313Hydrochloric AcidHCID 57786525HCID 57786525, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of tert-butyl (2R,3S)-4-cyclohexyl-2-hydroxy-3-(2-(3-((3-methoxypropoxy)-(phenyl)methyl)piperidin-1-yl)-3,4-dioxocyclobut-1-enylamino)butylcarbamate (37 mg, 0.06 mmol) was dissolved in dioxane (1 mL) and treated with 4M HCl in dioxane (1 mL). The reaction was allowed to stir for 3 h. Evaporation of the solvent provided 3-((2S,3R)-4-amino-1-cyclohexyl-3-hydroxybutan-2-ylamino)-4-(3-((3-methoxypropoxy)(phenyl)methyl)piperidin-1-yl)cyclobut-3-ene-1,2-dione as its HCl salt (32 mg); MS m/z 528 (M+H+).

Workup

  1. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f4e9442320444a829d7ebc72afc0abd5
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Reaction notes

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