HCID 10269592, compound → HCID 87830570, compound

HRID 1006863Notes

Reaction equation

HRID 1006863 reaction equation
[CH3:1][S:2]([N:5]1[C@H:9]([CH2:10][O:11][CH2:12][C:13]2[CH:18]=[C:17]([F:19])[C:16]([F:20])=[CH:15][C:14]=2[F:21])[CH2:8][C@@H:7]([SH:22])[CH2:6]1)(=[O:4])=[O:3].[NH:23]([C:40]([CH3:42])=[O:41])[C@H:24]([C:37]([OH:39])=[O:38])[CH2:25][S:26]SC1N=CC=CC=1[N+]([O-])=O>>[C:40]([NH:23][C@@H:24]([CH2:25][S:26][S:22][C@@H:7]1[CH2:8][C@@H:9]([CH2:10][O:11][CH2:12][C:13]2[CH:18]=[C:17]([F:19])[C:16]([F:20])=[CH:15][C:14]=2[F:21])[N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:6]1)[C:37]([OH:39])=[O:38])(=[O:41])[CH3:42]

Participants

3

Reactant 2

HCID 10269592HCID 10269592, compoundHCID 90941662HCID 90941662, compound

Product 1

HCID 87830570HCID 87830570, compoundYield 93.3%

Procedure

(3R,5S)-1-Methanesulfonyl-5-(2,4,5-trifluoro-benzyloxymethyl)-pyrrolidine-3-thiol (100 mg, 0.28 mmol) and Ac-Cys(Npys)-OH (89 mg, 0.28 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. Work-up as above (Example 22a) yielded (R)-2-acetylamino-3-[(3R,5S)-1-methanesulfonyl-5-(2,4,5-trifluoro-benzyloxymethyl)-pyrrolidin-3-yldisulfanyl]-propionic acid (135 mg), MS: 515 (MH−).

Workup

  1. customdegassed DMF (abs. 2 ml)
  2. customdegassed 0.1 M phosphate buffer (pH 6.2, 2 ml)
  3. additionwas added

Sources & evidence

ORD record
ord-06429b68e6fc4fc18af20a3f6a1f8965
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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