Hydrochloric Acid → HCID 90082519, compound

HRID 1486043Notes

Reaction equation

HRID 1486043 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([O:48][CH3:49])=[C:7]2[CH2:12][N:13]1[C:19](=[O:20])[C@@H:18]([NH:21][C:22](=[O:34])[C@@H:23]([N:25](C)[C:26](=O)OC(C)(C)C)[CH3:24])[C@H:17]([CH3:35])[N:16]([C:36]([CH:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)=[O:37])[C:15]2[CH:44]=[CH:45][CH:46]=[CH:47][C:14]1=2.[ClH:50]>CO.C(OCC)C>[ClH:50].[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([O:48][CH3:49])=[C:7]2[CH2:12][N:13]1[C:19](=[O:20])[C@@H:18]([NH:21][C:22](=[O:34])[C@@H:23]([NH:25][CH3:26])[CH3:24])[C@H:17]([CH3:35])[N:16]([C:36]([CH:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)=[O:37])[C:15]2[CH:44]=[CH:45][CH:46]=[CH:47][C:14]1=2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118292590HCID 118292590, compound

Product 1

HCID 90082519HCID 90082519, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of tert-butyl(S)-1-((3S,4S)-1-((5-bromo-2-methoxynaphthalen-1-yl)methyl)-4-methyl-2-oxo-5-(tetrahydro-2H-pyran-4-carbonyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (45 mg, 61 μmol) in methanol (500 μl) at room temperature was treated with a 2 M hydrochloric acid in diethyl ether solution (1.3 ml) and stirred for 3.5 h. The reaction was then concentrated in vacuo, dissolved in water and placed on a lyophilizer over night to afford (S)-N-((3S,4S)-1-((5-bromo-2-methoxynaphthalen-1-yl)methyl)-4-methyl-2-oxo-5-(tetrahydro-2H-pyran-4-carbonyl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-(methylamino)propanamide hydrochloride (36 mg, 88%) as a light yellow powder: LC-MS m/z 637 [M+H]+.

Workup

  1. concentrationThe reaction was then concentrated in vacuo
  2. dissolutiondissolved in water
  3. waitplaced on a lyophilizer over night

Sources & evidence

ORD record
ord-3c0e9ae71cf24f10950c998e55e39d58
Source dataset
uspto-grants-2016_08
Patent number
US09422331B2

Reaction notes

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