Hydrochloric Acid → (S)-3-(2-chloro-3-fluorobenzyl)-1-(1-hydroxypent-4-en-2-yl)-1-methylurea

HRID 340961Notes

Reaction equation

HRID 340961 reaction equation
[Si]([O:8][CH2:9][C@@H:10]([N:14]([CH3:27])[C:15]([NH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=1[Cl:26])=[O:16])[CH2:11][CH:12]=[CH2:13])(C(C)(C)C)(C)C.Cl>CO>[Cl:26][C:20]1[C:21]([F:25])=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][NH:17][C:15](=[O:16])[N:14]([C@@H:10]([CH2:11][CH:12]=[CH2:13])[CH2:9][OH:8])[CH3:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57947454(S)-1-(1-(tert-butyldimethylsilyloxy)pent-4-en-2-yl)-3-(2-chloro-3-fluorobenzyl)-1-methylurea

Product 1

HCID 57947623(S)-3-(2-chloro-3-fluorobenzyl)-1-(1-hydroxypent-4-en-2-yl)-1-methylureaYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-1-(1-(tert-butyldimethylsilyloxy)pent-4-en-2-yl)-3-(2-chloro-3-fluorobenzyl)-1-methylurea (5.80 g, 10.8 mmol) in MeOH (50 mL) was added HCl (1N, 32.0 mL). The resulting solution was stirred at RT for 30 min. The mixture was partially concentrated and filtered. The filtrate was purified on RP-HPLC using a mixture of acetonitrile and water to give (S)-3-(2-chloro-3-fluorobenzyl)-1-(1-hydroxypent-4-en-2-yl)-1-methylurea (2.0 g, 77%) as a white solid, which was used without further purification. LRMS (M+H+) m/z 301.2.

Workup

  1. concentrationThe mixture was partially concentrated
  2. filtrationfiltered
  3. customThe filtrate was purified on RP-HPLC
  4. additiona mixture of acetonitrile and water

Sources & evidence

ORD record
ord-4e51b4ddf1e747bab6f388cd19b8b60a
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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