Triethylamine → HCID 131715794, compound

HRID 414172Notes

Reaction equation

HRID 414172 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([NH:14][C@H:15]([C:19]([OH:21])=O)[CH:16]([CH3:18])[CH3:17])(=[O:13])=[O:12].C(N(CC)CC)C.ClC(OCC(C)C)=O.[C:37]([C:39]1[CH:55]=[CH:54][C:42]([CH2:43][C@@H:44]([C:46]([N:48]2[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]2)=[O:47])[NH2:45])=[CH:41][CH:40]=1)#[N:38]>ClCCl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([NH:14][CH:15]([C:19]([NH:45][C@H:44]([C:46]([N:48]1[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]1)=[O:47])[CH2:43][C:42]1[CH:41]=[CH:40][C:39]([C:37]#[N:38])=[CH:55][CH:54]=1)=[O:21])[CH:16]([CH3:18])[CH3:17])(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 730259HCID 730259, compoundHCID 22858565HCID 22858565, compound

Product 1

HCID 131715794HCID 131715794, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 7 g (0.023 mole) of N-betanaphthylsulphonylvaline (III: R1 =CH(CH3)2 ; Ar=betanaphthyl) racemic (RS) in 10 ml of dichloromethane, kept at between 0° and +5° C., 2.6 g (0.023 mole) triethylamine is added, then 3.4 g (0.025 mole) of isobutyl chloroformate is added drop by drop, and the whole is left for one hour at this temperature. Then 6.2 g (0.024 mole) of 1-(p-cyanophenylalanyl)piperidine (II: NR2R3 =piperidino) dissolved in 50 ml of dichloromethane is added, and the reactional medium is left for 20 hours at ambient temperature. After evaporating to dryness, the residue is taken up with water. The aqueous phase is extracted with dichloromethane. The organic extracts are dried on anhydrous sodium sulphate and evaporated to dryness. The oily residue is purified by chromatography on a silica column (elution: toluene-ethyl acetate, 1:1).

Workup

  1. customkept at between 0° and +5° C.
  2. additionis added
  3. waitthe reactional medium is left for 20 hours at ambient temperature
  4. customAfter evaporating to dryness
  5. extractionThe aqueous phase is extracted with dichloromethane
  6. dry with materialThe organic extracts are dried on anhydrous sodium sulphate
  7. customevaporated to dryness
  8. customThe oily residue is purified by chromatography on a silica column (elution: toluene-ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-75e236b2525e4ced97f6c9eef6de53c4
Source dataset
uspto-grants-1988_12
Patent number
US04791102

Reaction notes

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