Diethyl Ether → HCID 54320917, compound

HRID 231871Notes

Reaction equation

HRID 231871 reaction equation
C1(=O)N(N([C:11](=[O:22])[CH2:12][S:13][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)CC([O-])=O)C(=O)CC1.[NH2:25][C@@H:26]([C:28]([NH:30][CH2:31][C:32]([NH:34][CH2:35][C:36]([OH:38])=[O:37])=[O:33])=[O:29])[CH3:27].C(OCC)C>C(O)C.O>[C:14]([S:13][CH2:12][C:11]([NH:25][C@@H:26]([C:28]([NH:30][CH2:31][C:32]([NH:34][CH2:35][C:36]([OH:38])=[O:37])=[O:33])=[O:29])[CH3:27])=[O:22])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 154942777286-90-9HCID 86743235HCID 86743235, compound

Product 1

HCID 54320917HCID 54320917, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1 g of succinimidyl-N-(S-benzoylmercaptoacetyl)glycinate in 25 ml of anhydrous ethanol at 70° C. is added in one portion a solution of 203 mg of D-alanylglycylglycine in 10 ml of water at 70° C. The reaction mixture is refluxed for 1 hour and the solvents are evaporated under reduced pressure. The residue is agitated with 5 portions of 25 ml acetone, which is isolated by filtration. The combined filtrates are treated with diethylether until precipitation is complete. The precipitate is filtered off, washed with diethylether and dried over P2O5 under vacuum to obtain 170 mg (47,7%) of S-benzoylmercaptoacetyl-d-alanylglycylglycine as a white powder, m.p. 167°-170° C. [α]D20 +22 (c=1 in methanol); nmr (DMSO-d6): δ 1.24 (3H, d, CH3), 3.88 (2H, s, CH2 --S), 3.74 (4H, d, 2×CH2 --N), 4.31 (1H, q, CH), 8.08 and 8.24 (each 1H, t, α-- and β--NH), 8.51 (1H, d, δ--NH), 7.5-8.04 (5H, complex, aromatic).

Workup

  1. temperatureThe reaction mixture is refluxed for 1 hour
  2. customthe solvents are evaporated under reduced pressure
  3. customwhich is isolated by filtration
  4. filtrationThe precipitate is filtered off
  5. washwashed with diethylether
  6. dry with materialdried over P2O5 under vacuum

Sources & evidence

ORD record
ord-c692cea4e0af41ec8901ffad7793eb23
Source dataset
uspto-grants-1989_07
Patent number
US04849511

Reaction notes

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