Hydrochloric Acid → HCID 118160645, compound

HRID 1048870Notes

Reaction equation

HRID 1048870 reaction equation
C(OC([N:8]1[C:12]([CH2:13][CH:14]([C:28]([S:30][CH2:31][CH:32]([NH:37][C:38](=[O:40])[CH3:39])[C:33]([O:35][CH3:36])=[O:34])=[O:29])[NH:15][C:16](=[O:27])[CH2:17][CH2:18][NH:19]C(OC(C)(C)C)=O)=[CH:11][N:10]=[CH:9]1)=O)(C)(C)C.[ClH:41]>O1CCOCC1>[ClH:41].[ClH:41].[C:38]([NH:37][C@@H:32]([CH2:31][S:30][C:28](=[O:29])[C@@H:14]([NH:15][C:16](=[O:27])[CH2:17][CH2:18][NH2:19])[CH2:13][C:12]1[NH:8][CH:9]=[N:10][CH:11]=1)[C:33]([O:35][CH3:36])=[O:34])(=[O:40])[CH3:39]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118160639HCID 118160639, compound

Product 1

HCID 118160645HCID 118160645, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

5-[2-(2-Acetylamino-2-methoxycarbonyl-ethylsulfanylcarbonyl)-2-(3-tert-butoxycarbonylamino-propionylamino)-ethyl]-imidazole-1-carboxylic acid tert-butyl ester (46a, 0.1028 g, 0.175 mmol) in dry dioxane (2 mL) was added dropwise to 4N HCl in dioxane (5.0 mL, 114 mmol) and the mixture was stirred about 2 hours at room temperature. The reaction mixture was concentrated to dryness and residual volatiles removed in high vacuum. The product was obtained as a white solid. MS: (M+1)+=386.1. 1H NMR (DMSO-d6) δ 9.15 (bm, 1H), 9.11 (s, 1H), 8.48 (bs, 1H), 8.00 (bm, 3H), 7.44 (bs, 1H), 4.69 (bm, 1H), 4.37 (bm, 1H), 3.64-3.56 (bm, 5H), 3.4-3.1 (bm, number of protons obscured by water peak and residual dioxane), 2.93 (bs, 2H), 2.58 (bm, 2H), 1.85, (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness and residual volatiles
  2. customremoved in high vacuum
  3. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-1999403397b34db8a38bd196fc3f82dd
Source dataset
uspto-grants-2016_07
Patent number
US09382211B2

Reaction notes

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