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

HRID 416393Notes

Reaction equation

HRID 416393 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-70cda33478a74f24b7e667ff971c2084
Source dataset
uspto-grants-2012_01
Patent number
US08088793B2

Reaction notes

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