Tritylamine → Fmoc-Asn(Trt)-OH

HRID 1110191

Reaction equation

HRID 1110191 reaction equation
ClC(N(C)C)=C(C)C.[NH:9]([C:25]([O:27][CH2:28][CH:29]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35]2[C:30]1=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:26])[C@H:10]([C:15]([O:17]CC1C=CC=CC=1)=[O:16])[CH2:11][C:12](=[O:14])O.[C:42]([NH2:61])([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>ClCCCl.C(OCC)(=O)C>[NH:9]([C:25]([O:27][CH2:28][CH:29]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:36]2[C:41]1=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:26])[C@H:10]([C:15]([OH:17])=[O:16])[CH2:11][C:12](=[O:14])[NH:61][C:42]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)[C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1

Participants

6

Reactant 3

HCID 138598TritylamineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 11224591Fmoc-Asp-OBzl

Product 1

HCID 640248Fmoc-Asn(Trt)-OH

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

0.8 ml of 1-chloro-N,N,2-trimethyl-prop-1-enylamine (A. Devos et al., J. Chem. Soc., Chem. Commun., Vol. 1979, p. 1180) is added to a stirred solution of 2.09 g of Fmoc-Asp-OBzl in 20 ml of 1,2-dichloroethane at 0° under an argon atmosphere. After 10 minutes, a solution of 1.2 g of tritylamine in 4 ml of 1,2-dichloroethane is added, and then the mixture is stirred for 2 hours, diluted with ethyl acetate and washed with water. The organic phase is dried and evaporated. The residue is taken up in chloroform and chromatographed on 250 g of silica gel. The fractions containing the Fmoc-Asn(Trt)-OBzl are combined and evaporated; the product is obtained as an amorphous foam.

Workup

  1. washwashed with water
  2. customThe organic phase is dried
  3. customevaporated
  4. customchromatographed on 250 g of silica gel
  5. additionThe fractions containing the Fmoc-Asn(Trt)-OBzl
  6. customevaporated
  7. customthe product is obtained as an amorphous foam

Sources & evidence

ORD record
ord-77092f084bd54ee4913616dde60a2a08
Source dataset
uspto-grants-1994_06
Patent number
US05324833

Linked notes

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