4-Nitrophenyl formate → HCID 59543533, compound

HRID 1697519Notes

Reaction equation

HRID 1697519 reaction equation
Cl.[C:2]([C:4]1([NH:7][C:8]([C@@H:10]2[CH2:14][C@@H:13]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])(=[O:17])=[O:16])[CH2:12][NH:11]2)=[O:9])[CH2:6][CH2:5]1)#[N:3].C(N(CC)C(C)C)(C)C.[CH:34](OC1C=CC([N+]([O-])=O)=CC=1)=[O:35]>C(#N)C>[C:2]([C:4]1([NH:7][C:8]([C@@H:10]2[CH2:14][C@@H:13]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])(=[O:17])=[O:16])[CH2:12][N:11]2[CH:34]=[O:35])=[O:9])[CH2:6][CH2:5]1)#[N:3]

Participants

5

Reactant 3

HCID 746284-Nitrophenyl formateHCID 81531DiisopropylethylamineHCID 66770259HCID 66770259, compound

Product 1

HCID 59543533HCID 59543533, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To as solution of (2S,4R)-4-(2-chloro-benzenesulfonyl)-pyrrolidine-2-carboxylic acid (1-cyano-cyclopropyl)-amide hydrochloride (0.12 mmole) from experiment K4 in acetonitrile (1.0 ml) was added at 22° C. N,N-diisopropylethyl amine (0.38 mmole) and p-nitrophenyl formate (0.14 mmole) and stirring was continued for 2 h. The mixture was evaporated, the residue partitioned between ethyl acetate and aqueous sodium carbonate, the organic layer was washed with water, dried and evaporated. The residue was purified by prep. HPLC (RP-18) using a mixture of acetonitrile and water to give (2S,4R)-4-(2-chloro-benzenesulfonyl)-1-formyl-pyrrolidine-2-carboxylic acid (1-cyano-cyclopropyl)-amide as a colorless oil. MS: 482.3 [M+H]+.

Workup

  1. customThe mixture was evaporated
  2. customthe residue partitioned between ethyl acetate and aqueous sodium carbonate
  3. washthe organic layer was washed with water
  4. customdried
  5. customevaporated
  6. customThe residue was purified by prep
  7. additiona mixture of acetonitrile and water

Sources & evidence

ORD record
ord-8f623224799d4e4f933c426de5d7173c
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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