Hydrochloric Acid → 228581-97-3

HRID 343314Notes

Reaction equation

HRID 343314 reaction equation
[OH-].[Na+].Cl.C([O:6][C:7]([C@H:9]1[CH2:14][C:13]([CH3:15])=[CH:12][CH2:11][N:10]1[C:16](=[O:43])[C@H:17]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([C:40](=[NH:42])[NH2:41])[CH:35]=1)[NH:18][S:19]([C:22]1[CH:31]=[C:30]2[C:25]([CH2:26][CH2:27][N:28]([CH3:32])[CH2:29]2)=[CH:24][CH:23]=1)(=[O:21])=[O:20])=[O:8])C.Cl>O1CCOCC1>[CH3:15][C:13]1[CH2:14][C@H:9]([C:7]([OH:8])=[O:6])[N:10]([C:16](=[O:43])[C@H:17]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:40](=[NH:41])[NH2:42])[CH:35]=2)[NH:18][S:19]([C:22]2[CH:31]=[C:30]3[C:25]([CH2:26][CH2:27][N:28]([CH3:32])[CH2:29]3)=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH2:11][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 70095416HCID 70095416, compound

Product 1

HCID 9958912228581-97-3Yield 101.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1M Aqueous sodium hydroxide solution (16.4 ml, 16.4 mmol) was added to a stirred solution of 4-methyl-1-[N-(2-methyl-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl)-3-amidino-(S)-phenylalanyl]-1,2,3,6-tetrahydropyridine-2(R)-carboxylic acid ethyl ester hydrochloride (Preparation 67; 1.99 g, 3.29 mmol) in 1,4-dioxan (15 ml). After 3.5 hours at room temperature, the excess sodium hydroxide was carefully neutralised by the dropwise addition of 1M hydrochloric acid and the resulting clear solution evaporated to dryness under reduced pressure. The residue was extracted with a hot mixture of dichloromethane and 2-propanol (1:1), then the extract filtered and the filtrate evaporated under reduced pressure to afford the title compound (1.80 g) as a white solid. Rf 0.12 (SS 13). [α]D25 +44° (c=0.1, C3OH). Found: C,55.75; H,6.34; N,11.01. C27H33N5O5S; 2.50 H2O; 0.50 (CH3)2CHOH requires C,55.62; H,6.49; N,10.99%.

Workup

  1. customthe resulting clear solution evaporated to dryness under reduced pressure
  2. extractionThe residue was extracted with a hot mixture of dichloromethane and 2-propanol (1:1)
  3. filtrationthe extract filtered
  4. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-d1a49555327748388c992d1d4c5aeaa4
Source dataset
uspto-grants-1999_01
Patent number
US05861393

Reaction notes

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