1,2-Dichloroethane → HCID 23382104, compound

HRID 1281186Notes

Reaction equation

HRID 1281186 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]([NH:12][C@H:13]([C:18]([OH:20])=O)[C:14]([CH3:17])([CH3:16])[CH3:15])=[O:11].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[N:35]1([C:40]2[CH:45]=[CH:44][C:43]([CH2:46][N:47]([NH:60][C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])[CH2:48][C@H:49]([OH:59])[C@@H:50]([NH2:58])[CH2:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)=[CH:42][CH:41]=2)[CH2:39][CH2:38][CH2:37][CH2:36]1>CN(C=O)C>[N:35]1([C:40]2[CH:45]=[CH:44][C:43]([CH2:46][N:47]([NH:60][C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])[CH2:48][C@H:49]([OH:59])[C@@H:50]([NH:58][C:18](=[O:20])[C@H:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[NH:12][C:10]([O:9][CH3:8])=[O:11])[CH2:51][C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)=[CH:42][CH:41]=2)[CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 11263950N-(Methoxycarbonyl)-L-tert-leucineHCID 23382102HCID 23382102, compound

Product 1

HCID 23382104HCID 23382104, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

12.3 ml (88 mmol) of triethylamine are added to a solution of 3.3 g (17.6 mmol) of N-methoxycarbonyl-(L)-tert-leucine, 6.7 g (35.2 mmol) of EDC and 4.8 g (35.2 mmol) of HOBT in 90 ml of DMF (degassed under vacuum) and the whole is stirred at RT for 20 min. After that, 4 g (8.8 mmol) of 1-[p-(pyrrolidin-1-yl)phenyl]-4(S)-hydroxy-2-(tert-butyloxycarbonyl)amino-5(S)-amino-6-phenyl-2-azahexane (Example 8d), dissolved in 20 ml of DMF, are added and the mixture is stirred at RT for 16 h. The reaction mixture is concentrated by evaporation and the residue is taken up in ethyl acetate/water. The organic phase is separated off and subsequently washed consecutively with water, 5% sodium bicarbonate solution (twice), water, dilute brine and brine, with the title compound thereby being obtained. The solvent is removed and the residue is recrystallized from ether in an ice bath, with the title compound thereby being obtained.

Workup

  1. additionare added
  2. stirringthe mixture is stirred at RT for 16 h
  3. concentrationThe reaction mixture is concentrated by evaporation
  4. customThe organic phase is separated off
  5. washsubsequently washed consecutively with water, 5% sodium bicarbonate solution (twice), water, dilute brine and brine

Sources & evidence

ORD record
ord-6c89e1bd30db4213880a314ba64cb6b3
Source dataset
uspto-grants-2002_09
Patent number
US06451973B1

Reaction notes

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