Ethyl Acetate → HCID 178521045, compound

HRID 1264400Notes

Reaction equation

HRID 1264400 reaction equation
[C:1]([CH2:3][CH2:4][N:5]([CH:46]1[CH2:48][CH2:47]1)[C:6]([C@@H:8]1[CH2:12][C@@H:11]([S:13][C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][N:9]1[S:33]([C:36]1[CH:45]=[CH:44][C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=1)(=[O:35])=[O:34])=[O:7])#[N:2].[NH4+].[Cl-].[N-:51]=[N+:52]=[N-:53].[Na+].CCOC(C)=O>CN(C=O)C.O>[CH:46]1([N:5]([CH2:4][CH2:3][C:1]2[NH:53][N:52]=[N:51][N:2]=2)[C:6]([C@@H:8]2[CH2:12][C@@H:11]([S:13][C:14]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:10][N:9]2[S:33]([C:36]2[CH:45]=[CH:44][C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH:37]=2)(=[O:35])=[O:34])=[O:7])[CH2:47][CH2:48]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 86758901HCID 86758901, compound

Product 1

HCID 178521045HCID 178521045, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 336 mg (0.5 mmol) (2S,4R)-1-(Naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine-2-carboxylic acid (2-cyano-ethyl)-cyclopropyl-amide, 267 mg (5 mmol) NH4Cl and 325 mg (5 mmol) NaN3 in 10 ml DMF were heated at 70° C. for 22 h. 267 mg (5 mmol) NH4Cl and 325 mg (5 mmol) NaN3 together with 40 ml DMF were added and heated at 100° C. (24h) and at 120° C. (24h). The reaction was poured in H2O (0° C.)/EtOAc (3×). The organic phases were washed with aqueous 10% KHSO4, 10% NaCl solution and dried over Na2SO4. Purification by flash-chromatography on silicagel (CH2Cl2/MeOH: 99:1) gave 143 mg (40%) (2S,4R)-1-(Naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine-2-carboxylic acid cyclopropyl-[2-(1H -tetrazol-5-yl)-ethyl]-amide, MS: 715 (MH+).

Workup

  1. customat 120° C.
  2. washThe organic phases were washed with aqueous 10% KHSO4, 10% NaCl solution
  3. dry with materialdried over Na2SO4
  4. customPurification by flash-chromatography on silicagel (CH2Cl2/MeOH: 99:1)

Sources & evidence

ORD record
ord-3b56f828279048abbd6b837c0f680c83
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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