Water → Hydrochloric Acid

HRID 235728Notes

Reaction equation

HRID 235728 reaction equation
[Cl:1][C:2]1[CH:42]=[CH:41][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10]([CH2:19][C:20]([NH:22][CH2:23][CH:24]([OH:39])[CH2:25][NH:26][C:27](=[O:38])[C@H:28]([CH3:37])[NH:29]C(OC(C)(C)C)=O)=[O:21])=[C:9]2[CH3:40])=[O:7])=[CH:4][CH:3]=1.O>C(OCC)(=O)C>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10]([CH2:19][C:20]([NH:22][CH2:23][CH:24]([OH:39])[CH2:25][NH:26][C:27](=[O:38])[C@H:28]([CH3:37])[NH2:29])=[O:21])=[C:9]2[CH3:40])=[O:7])=[CH:41][CH:42]=1

Participants

5

Reactant 2

HCID 962WaterHCID 13772570HCID 13772570, compound

Product 2

HCID 313Hydrochloric AcidHCID 13772572HCID 13772572, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

In a manner analogous to that described in Stage 25.3, from 1.44 g (2.38 mmol) of N-tert.-butoxycarbonyl-L-alanine-3-{2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-acetylamino}-2-hydroxypropylamide, containing 0.21 mol of water, in 40 ml of ethyl acetate, with 40 ml of approximately 5N hydrochloric acid in ethyl acetate (2.5 hours, 0°), there is obtained L-alanine-3-{2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-acetylamino}-2-hydroxypropylamide hydrochloride in the form of yellowish crystals that decompose at 153° and above (made into a suspension from hot ethyl acetate) and contain 0.17 mol of water; [α]D20 =+5.8°±1.0° (c=1.043; methanol), Rf =0.22 (chloroform:methanol=7:3).

Sources & evidence

ORD record
ord-273c813b8d704c0684153b629b314a74
Source dataset
uspto-grants-1987_02
Patent number
US04640911

Reaction notes

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