4-Methoxybenzenesulfonyl chloride → HCID 69543905, compound

HRID 1278999Notes

Reaction equation

HRID 1278999 reaction equation
[CH2:1]([NH:8][NH:9][C:10]([C@@H:12]1[CH2:16][C@@H:15]([S:17][C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][N:13]1[S:37]([C:40]1[CH:49]=[CH:48][C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:41]=1)(=[O:39])=[O:38])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[CH3:59][O:60][C:61]1[CH:66]=[CH:65][C:64]([S:67](Cl)(=[O:69])=[O:68])=[CH:63][CH:62]=1>C(Cl)Cl>[CH2:1]([N:8]([S:67]([C:64]1[CH:63]=[CH:62][C:61]([O:60][CH3:59])=[CH:66][CH:65]=1)(=[O:69])=[O:68])[NH:9][C:10]([C@@H:12]1[CH2:16][C@@H:15]([S:17][C:18]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:14][N:13]1[S:37]([C:40]1[CH:49]=[CH:48][C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:41]=1)(=[O:39])=[O:38])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chloride2×HCID 81531Diisopropylethylamine2×HCID 69543783HCID 69543783, compound

Product 1

HCID 69543905HCID 69543905, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(step 12) To 200 mg (0.3 mmol) (2S,4R)-1-(Naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine-2-carboxylic acid N′-benzyl-hydrazide in 3 ml CH2Cl2 were added 60 μl (0.35 mmol, 1.2 eq) N,N-diisopropylethylamine, 72.5 mg (0.35 mmol, 1.2 eq) 4-methoxybenzene sulfonylchloride and 22.5 mg (0.12 eq) DMAP-poly at 0° C. The suspension was shaken at RT for 3 days, additional 25 μl (0.15 mmol, 0.5 eq) N,N-diisopropylethylamine, 31 mg (0.15 mmol, 0.5 eq) 4-methoxybenzene sulfonylchloride and 22.5 mg (0.12 eq) DMAP-poly were added and the reaction was continued for a day. After filtration and washing of the resin with CH2Cl2, the organic phase was concentrated and the crude material purified by flash chromatography yielding 152 mg (61%) (2S,4R)-1-(Naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine-2-carboxylic acid N′-benzyl-N′-(4-methoxy-benzenesulfonyl)-hydrazide which was directly subjected to the following reaction.

Workup

  1. waitthe reaction was continued for a day
  2. filtrationAfter filtration
  3. washwashing of the resin with CH2Cl2
  4. concentrationthe organic phase was concentrated
  5. customthe crude material purified by flash chromatography

Sources & evidence

ORD record
ord-b9a1cde6954c41d990c4e1115f0d6c73
Source dataset
uspto-grants-2002_09
Patent number
US06444829B1

Reaction notes

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