Hydrochloric Acid → HCID 11386104, compound

HRID 1246353Notes

Reaction equation

HRID 1246353 reaction equation
C([O:3][C:4](=[O:34])[CH2:5][N:6]([CH2:19][CH2:20][NH:21][S:22]([C:25]1[S:26][C:27]2[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=2[N:29]=1)(=[O:24])=[O:23])[C:7](=[O:18])[CH2:8][N:9]1[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]1=[O:11])C.O.[OH-].[Li+].Cl>O1CCCC1.O>[S:26]1[C:27]2[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=2[N:29]=[C:25]1[S:22]([NH:21][CH2:20][CH2:19][N:6]([C:7](=[O:18])[CH2:8][N:9]1[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]1=[O:11])[CH2:5][C:4]([OH:34])=[O:3])(=[O:23])=[O:24]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 21868441HCID 21868441, compound

Product 1

HCID 11386104HCID 11386104, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-[2-(Benzothiazole-2-sulfonylamino)-ethyl]-N-[(thymin-1-yl)-acetyl]-glycine ethyl ester (5.10 g, 10 mmol) was suspended in tetrahydrofuran (20 mL) and the solution of lithium hydroxide monohydrate (1.03 g, 25 mmol) in water (20 mL) was added. The reaction mixture was stirred for 1 h. at ambient temperature. The aqueous solution was acidified by the dropwise addition of 1N HCl at 0° C. The title compound was extracted with ethyl acetate (3×10 mL), the combined extracts were dried over magnesium sulfate and filtered. The filtrate was evaporated to dryness in vacuo to afford the desired product (4.57 g, 95%). 1H NMR (500 MHz; DMSO-d6) δ 11.30 (s, 0.6H), 11.28 (s, 0.4H), 8.88 (s, 0.6H), 8.77 (s, 0.4H), 8.27 (d, 1H), 8.18 (d, 1H), 7.69˜7.64 (m, 2H), 7.31 (s, 0.6H), 7.23 (s, 0.4H), 4.64 (s, 1.2H), 4.45 (s, 0.8H), 4.21 (s, 0.8H), 3.98 (s, 1.2H), 3.52 (t, 1.2H), 3.38 (s, 2H), 3.21 (t, 0.8H), 1.73 (s, 3H).

Workup

  1. extractionThe title compound was extracted with ethyl acetate (3×10 mL)
  2. dry with materialthe combined extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-12dc5dcfca7c496da76b0a5691806fcd
Source dataset
uspto-grants-2006_10
Patent number
US07125994B2

Reaction notes

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