Diisopropylethylamine → HCID 86759235, compound

HRID 479626Notes

Reaction equation

HRID 479626 reaction equation
C[O:2][C:3](=[O:33])[C@:4](C)([C:25](=[O:31])[C@@H:26]1[CH2:30][CH2:29][CH2:28][NH:27]1)[C@H:5]([NH:13][S:14]([C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=1)(=[O:16])=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.C[CH2:35][N:36]([CH:40]([CH3:42])C)[CH:37]([CH3:39])C.C(=O)(O)[O-:44].[Na+]>C(Cl)Cl>[Cl:24][C:19]1[CH:18]=[C:17]([S:14]([NH:13][C@@H:5]([C:6]2[CH:7]=[CH:8][C:9]([O:12][C:35]([N:36]3[CH2:37][CH2:39][CH2:42][CH2:40]3)=[O:44])=[CH:10][CH:11]=2)[C@@H:4]([C:25](=[O:31])[C@@H:26]2[CH2:30][CH2:29][CH2:28][NH:27]2)[C:3]([OH:2])=[O:33])(=[O:15])=[O:16])[CH:22]=[C:21]([Cl:23])[CH:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 86759236HCID 86759236, compound

Product 1

HCID 86759235HCID 86759235, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(3,5-Dichlorobenzenesulfonyl)-2-methyl-2(S)-prolyl-3(R)-amino-3-(4-hydroxyphenyl)propionic acid methyl ester, as prepared in Example 28, Step F (50 mg, 0.11 mmol), was dissolved in 1 mL of methylene chloride and treated sequentially at 0° with DIPEA (56 μl, 0.3 mmol) and chlorocarbonyl-N-pyrrolidine (16 mg, 0.12 mmol). The mixture was stirred for 1 hour, then worked up with saturated sodium bicarbonate, extracted with methylene chloride and dried over magnesium sulphate. The solution was filtered, solvent removed in vacuo and the product chromatographed on flash silica gel (70/30 hexane/ethyl acetate) (Rf=0.3). The methyl ester was recovered (42 mg) and subsequently hydrolysed by the procedure described in Example 39, Step F to N-(3,5-dichlorobenzenesulfonyl)-2(S)-prolyl-3(R)-amino-3-(4-(N-pyrrolidinylcarbonyloxy)phenyl)propionic acid (35 mg).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialdried over magnesium sulphate
  3. filtrationThe solution was filtered
  4. customsolvent removed in vacuo
  5. customthe product chromatographed on flash silica gel (70/30 hexane/ethyl acetate) (Rf=0.3)
  6. customThe methyl ester was recovered (42 mg)

Sources & evidence

ORD record
ord-1bf49051f54a46a181f512fd839f44e7
Source dataset
uspto-grants-2003_11
Patent number
US06645939B1

Reaction notes

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