Triethylamine → HCID 178512412, compound

HRID 726444Notes

Reaction equation

HRID 726444 reaction equation
[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].[C:8]([C:11]1[CH:38]=[CH:37][C:14]([O:15][CH2:16][CH2:17][CH2:18][C:19]([NH:21][CH2:22][C@H:23]([NH:27][S:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(=[O:30])=[O:29])[C:24]([OH:26])=[O:25])=[O:20])=[CH:13][CH:12]=1)(=[NH:10])[NH2:9].[CH2:39]([O:46][C:47](ON1C(=O)CCC1=O)=[O:48])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C(N(CC)CC)C>CN(C=O)C>[OH:3][C:2]([C:4]([F:7])([F:6])[F:5])=[O:1].[C:31]1([S:28]([NH:27][C@@H:23]([CH2:22][NH:21][C:19](=[O:20])[CH2:18][CH2:17][CH2:16][O:15][C:14]2[CH:37]=[CH:38][C:11]([C:8](=[NH:9])[NH:10][C:47]([O:46][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[O:48])=[CH:12][CH:13]=2)[C:24]([OH:26])=[O:25])(=[O:30])=[O:29])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 131720396HCID 131720396, compound

Product 1

HCID 178512412HCID 178512412, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the compound (51 mg) obtained in the above (1) in DMF (2 ml) are added N-(benzyloxycarbonyloxy)succinimide (25 mg) and triethylamine (14 μl), and the mixture is allowed to stand at room temperature for one day. The reaction mixture is concentrated under reduced pressure, and the residue is purified by HPLC, and the fractions containing the title compound are concentrated under reduced pressure. To the residue is added a mixture of 1N hydrochloric acid (2 ml) and acetic acid (2 ml), and the mixture is stirred at 50° C. for 13 hours. The reaction mixture is concentrated under reduced pressure, and the resultant is purified by HPLC to give the title compound (3 mg) as a white powder.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe residue is purified by HPLC
  3. additionthe fractions containing the title compound
  4. concentrationare concentrated under reduced pressure
  5. additionTo the residue is added
  6. additiona mixture of 1N hydrochloric acid (2 ml) and acetic acid (2 ml)
  7. concentrationThe reaction mixture is concentrated under reduced pressure
  8. customthe resultant is purified by HPLC

Sources & evidence

ORD record
ord-fd96943b0d1a407b92e7566f847ee55b
Source dataset
uspto-grants-1998_01
Patent number
US05707994

Reaction notes

Loading…