HCID 86585049, compound → HCID 18618394, compound

HRID 1264431Notes

Reaction equation

HRID 1264431 reaction equation
[SH:1][C@H:2]1[CH2:6][N:5]([S:7]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)(=[O:9])=[O:8])[C@H:4]([C:20]([N:22]([CH2:31][C:32]([OH:34])=[O:33])[CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:21])[CH2:3]1.[NH:35]([C:52]([CH3:54])=[O:53])[C@H:36]([C:49]([OH:51])=[O:50])[CH2:37][S:38]SC1N=CC=CC=1[N+]([O-])=O>>[C:52]([NH:35][CH:36]([CH2:37][S:38][S:1][CH:2]1[CH2:3][CH:4]([C:20](=[O:21])[N:22]([CH2:31][C:32]([OH:34])=[O:33])[CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:5]([S:7]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)(=[O:9])=[O:8])[CH2:6]1)[C:49]([OH:51])=[O:50])(=[O:53])[CH3:54]

Participants

3

Reactant 2

HCID 86585049HCID 86585049, compoundHCID 90941662HCID 90941662, compound

Product 1

HCID 18618394HCID 18618394, compound

Procedure

(2S,4R)-{[4-Mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carbonyl]-phenethyl-amino}-acetic acid (32.6 mg, 0.07 mmol) and Ac-Cys(Npys)—OH (20.6 mg, 0.07 mmol) were dissolved in argon-degassed DMF (abs. 2 ml) and degassed 0.1 M phosphate buffer (pH 6.2, 2 ml) was added. The reaction mixture was magnetically stirred for 2 h under argon. Ethyl acetate (30 ml), water (20 ml) were added and the organic phase was washed with water (3×20 ml) and concentrated under reduced pressure to give a yellow oil: 37 mg. Prep. RP-HPLC purification followed by pooling and freeze-drying of desired fractions yielded 2-acetylamino-3-[5-(carboxymethyl-phenethyl-carbamoyl)-1-(naphthalene-2-sulfonyl)-pyrrolidin-3-yldisulfanyl]-propionic acid as a white lyophilisate (20 mg) MS: 657.9 (M-H)−.

Workup

  1. customdegassed DMF (abs. 2 ml)
  2. customdegassed 0.1 M phosphate buffer (pH 6.2, 2 ml)
  3. additionwas added
  4. additionEthyl acetate (30 ml), water (20 ml) were added
  5. washthe organic phase was washed with water (3×20 ml)
  6. concentrationconcentrated under reduced pressure
  7. customto give a yellow oil
  8. customRP-HPLC purification
  9. customfreeze-drying of desired fractions

Sources & evidence

ORD record
ord-9aeb108e44694f2cbbcfff4461440007
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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