Ethanol → HCID 86585081, compound

HRID 1264430Notes

Reaction equation

HRID 1264430 reaction equation
[C:1]([S:4][C@H:5]1[CH2:9][N:8]([S:10]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)(=[O:12])=[O:11])[C@H:7]([C:23]([N:25]([CH2:34][C:35]([OH:37])=[O:36])[CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:24])[CH2:6]1)(=[O:3])[CH3:2].[CH3:38][CH2:39]O.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:38]([O:36][C:35](=[O:37])[CH2:34][N:25]([C:23]([C@@H:7]1[CH2:6][C@@H:5]([S:4][C:1](=[O:3])[CH3:2])[CH2:9][N:8]1[S:10]([C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1)(=[O:12])=[O:11])=[O:24])[CH2:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH3:39]

Participants

6

Reactant 3

HCID 702EthanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 86585080HCID 86585080, compound

Product 1

HCID 86585081HCID 86585081, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of 700 mg (1.29 mmol) (2S,4R)-{[4-Acetylsulfanyl-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carbonyl]-phenethyl-amino}-acetic acid and 0.1 ml (1.68 mmol) EtOH in 12 ml CH2Cl2 was treated at 0° C. with 273 mg (1.42 mmol) EDCI and 16 mg (0.13 mmol) DMAP. After warming up to RT (1 h), the reaction was partitioned between aqueous 10% KHSO4/Et2O (3×). The organic phases were washed with aqueous saturated KHCO3, 10% NaCl and dried over Na2SO4. Purification by flash-chromatography on silicagel (Hexane/EtOAc 9:1 to 4:1) gave 0.254 mg (34%) (2S,4R)-{[4-Acetylsulfanyl-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carbonyl]-phenethyl-amino}-acetic acid ethyl ester, mp: 119-120° C., MS: 569 (MH+).

Workup

  1. customthe reaction was partitioned between aqueous 10% KHSO4/Et2O (3×)
  2. washThe organic phases were washed with aqueous saturated KHCO3, 10% NaCl
  3. dry with materialdried over Na2SO4
  4. customPurification by flash-chromatography on silicagel (Hexane/EtOAc 9:1 to 4:1)

Sources & evidence

ORD record
ord-7f7d2781f0fc4f55b6ad9cb2306f7c6a
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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