Hydrochloric Acid → (S)-tert-butyl 4-(4-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-5-hydroxypentanoyl)piperazine-1-carboxylate

HRID 416452Notes

Reaction equation

HRID 416452 reaction equation
[Si]([O:8][CH2:9][C@@H:10]([N:28]([CH3:41])[C:29]([NH:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[C:34]=1[Cl:40])=[O:30])[CH2:11][CH2:12][C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)=[O:14])(C(C)(C)C)(C)C.Cl.C([O-])(O)=O.[Na+]>CO>[Cl:40][C:34]1[C:35]([F:39])=[CH:36][CH:37]=[CH:38][C:33]=1[CH2:32][NH:31][C:29](=[O:30])[N:28]([C@H:10]([CH2:9][OH:8])[CH2:11][CH2:12][C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[CH2:17][CH2:16]1)=[O:14])[CH3:41]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 57947925(S)-tert-butyl 4-(5-(tert-butyldimethylsilyloxy)-4-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)pentanoyl)piperazine-1-carboxylate

Product 1

HCID 57947492(S)-tert-butyl 4-(4-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-5-hydroxypentanoyl)piperazine-1-carboxylateYield 99.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-tert-butyl 4-(5-(tert-butyldimethylsilyloxy)-4-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)pentanoyl)piperazine-1-carboxylate (4.2 g, 6.8 mmol, 1.0 equiv.) in MeOH (35 mL), was added HCl (2N, 0.68 mL, 1.36 mmol, 0.2 equiv.). The reaction was stirred at RT for 1 h. NaHCO3 (1.1 g, 13.6 mmol, 2.0 equiv) was added to quench the reaction. The solvents were removed. The residue was dissolved in EtOAc (100 mL). The salt was filtered off and the filtrate was concentrated to give (S)-tert-butyl 4-(4-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-5-hydroxypentanoyl)piperazine-1-carboxylate (3.4 g, quant.). LRMS (M+H+) m/z 501.2.

Workup

  1. customto quench
  2. customthe reaction
  3. customThe solvents were removed
  4. dissolutionThe residue was dissolved in EtOAc (100 mL)
  5. filtrationThe salt was filtered off
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5d591f7ceb94495fbec85e70e9bb055a
Source dataset
uspto-grants-2012_01
Patent number
US08088793B2

Reaction notes

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