Triethylamine → BOC-(D)Trp-Lys(Z)-OMe

HRID 1903338Notes

Reaction equation

HRID 1903338 reaction equation
CCN(CC)CC.C1C=CC2N(O)N=NC=2C=1.[NH:18]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C@@H:19]([C:30]([OH:32])=O)[CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1.[NH2:40][C@H:41]([C:57]([O:59][CH3:60])=[O:58])[CH2:42][CH2:43][CH2:44][CH2:45][NH:46][C:47]([O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:48].Cl>CN(C=O)C.CCOC(C)=O.C(OCC)C>[NH:18]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C@@H:19]([C:30]([NH:40][C@H:41]([C:57]([O:59][CH3:60])=[O:58])[CH2:42][CH2:43][CH2:44][CH2:45][NH:46][C:47]([O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:48])=[O:32])[CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 111050N-((tert-Butoxy)carbonyl)-D-tryptophanHCID 1293537127894-50-4

Product 1

HCID 13391303BOC-(D)Trp-Lys(Z)-OMe

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 21584169Diethylether ethylacetateSolvent

Conditions

Temperature
-15 °C

Procedure

9.8 ml NEt3, 11.8 g HOBT and 21.3 g BOC-(D)Trp-OH are added to 23.3 g H-Lys(Z)-OMe hydrochloride in 300 ml DMF, and the solution cooled to -15° C. 15.6 g DDCI in 50 ml DMF are added and the reaction mixture stirred for ca. 16 hrs. at 0° C., followed by 2 hrs. at room temperature. The reaction mixture is diluted with AcOEt/ethyl-ether and the dicyclohexyl-urea is filtered off. The filtrate is washed with 2 N citric acid, H2O, 10% KHCO3 solution and 30% NaCl solution. The organic phase is dried over Na2SO4 and concentrated strongly under vacuum. Crystallisation is effected by the addition of ethyl-ether/hexane and the product is filtered off, washed with ethyl-ether/hexane and dried to yield the title compound:

Workup

  1. waitat 0° C., followed by 2 hrs
  2. customat room temperature
  3. filtrationthe dicyclohexyl-urea is filtered off
  4. washThe filtrate is washed with 2 N citric acid, H2O, 10% KHCO3 solution and 30% NaCl solution
  5. dry with materialThe organic phase is dried over Na2SO4
  6. concentrationconcentrated strongly under vacuum
  7. customCrystallisation
  8. additionis effected by the addition of ethyl-ether/hexane
  9. filtrationthe product is filtered off
  10. washwashed with ethyl-ether/hexane
  11. customdried

Sources & evidence

ORD record
ord-4016217a2ef747788aa2b7a97cf2fec0
Source dataset
uspto-grants-1984_03
Patent number
US04435385

Reaction notes

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