Hydrochloric Acid → HCID 57062134, compound

HRID 1460083Notes

Reaction equation

HRID 1460083 reaction equation
[CH3:1][C@@H:2]1[CH2:7][NH:6][C@@H:5]([CH3:8])[CH2:4][N:3]1[C@H:9]([C:24]1[CH:32]=[CH:31][C:27]([C:28]([O-:30])=[O:29])=[CH:26][CH:25]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][Si](C(C)(C)C)(C)C)[CH:11]=1.[Li+].[CH2:34](N1[C@@H](C)CN([C@@H](C2C=C(O)C=CC=2)C2C=CC(Cl)=CC=2)[C@H](C)C1)[CH:35]=[CH2:36].Cl>O1CCCC1>[CH2:36]([N:6]1[C@@H:5]([CH3:8])[CH2:4][N:3]([C@H:9]([C:24]2[CH:25]=[CH:26][C:27]([C:28]([OH:30])=[O:29])=[CH:31][CH:32]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=2)[C@H:2]([CH3:1])[CH2:7]1)[CH:35]=[CH2:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 57230267HCID 57230267, compoundHCID 131720130HCID 131720130, compound

Product 1

HCID 57062134HCID 57062134, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of crude lithium 4-((αR*)-α-((2R*,5S*)-2,5-dimethyl-1-piperazinyl)-3-tert-butyldimethylsiloxybenzyl)benzoate (11.5 g, from 23 mmol of Example 2 by the procedure of Example 6, Method B) in tetrahydrofuran was treated with 6M aqueous hydrochloric acid at room temperature for 18 hours. After dilution with water, the mixture was extracted with diethyl ether and the aqueous layer was adjusted to pH 8 with aqueous sodium hydroxide and extracted with dichloromethane. The aqueous layer was titrated to pH 6 with concentrated hydrochloric acid and the precipitated solid was collected by filtration, washed with water and dried under vacuum (60° C.) to give 2.65 g (30%) of (±)-4-((αR*)-α-((2R*,5S*)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)benzoic acid as an off-white powder. NMR (DMSO-d6) δ: 0.9 (d, J=6 Hz, 3H); 1.05 (d, J=6 Hz, 3H); 1.8 (dd, J1 =11 Hz, J2 =7 Hz, 1H); 2.1 (dd, J1 =11 Hz, J2 =7 Hz, 1H); 2.5 (m, 6H); 2.7 (d, J=11 Hz, 1H); 2.9 (dd, J1 =7 Hz, J2 =14 Hz); 3.1 (dd, J1 =14 Hz, J2 =5 Hz, 1H); 4.9-5.2 (m, 3H); 5.6-5.8 (m, 1H); 6.5 (dd, J1 =8 Hz, J2 =2 Hz, 1H); 6.8 (m, 2H); 7.1 (t, J=8 Hz, 1H); 7.3 (m, 1H); 7.4 (d, J=8 Hz, 2H); 7.9 (d, J=8 Hz, 2H). Calc. for C23H28N2O3 1.25 H2O: C, 68.55; H, 7.63; N, 6.95. Found: C, 68.61; H, 7.66; N, 7.02. Mass spectrum (Cl--CH4): m/z 381 (M+1, 44%), 153 (100%), 227 (17%).

Workup

  1. extractionAfter dilution with water, the mixture was extracted with diethyl ether
  2. extractionextracted with dichloromethane
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with water
  5. customdried under vacuum (60° C.)

Sources & evidence

ORD record
ord-39c5e44804444f998c03a60a13989247
Source dataset
uspto-grants-1998_12
Patent number
US05854249

Reaction notes

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