Trifluoroacetic acid → HCID 131714602, compound

HRID 246919Notes

Reaction equation

HRID 246919 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][C@H:9]([C:17]([NH:19][C@H:20]([C:24]([NH:26][C@H:27]([C:32]([NH:34][C@H:35]([C:38]([O:40][CH3:41])=[O:39])[CH2:36][OH:37])=[O:33])[CH2:28][C:29](=[O:31])[NH2:30])=[O:25])[C@@H:21]([CH3:23])[OH:22])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[NH:42]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[C@H:43]([C:48](ON1C(=O)CCC1=O)=[O:49])[C@H:44]([CH2:46][CH3:47])[CH3:45].C1C=CC2N(O)N=NC=2C=1.C(N1CCOCC1)C>CN(C=O)C>[NH:42]([C:58]([O:60][C:61]([CH3:63])([CH3:62])[CH3:64])=[O:59])[C@H:43]([C:48]([NH:8][C@H:9]([C:17]([NH:19][C@H:20]([C:24]([NH:26][C@H:27]([C:32]([NH:34][C@H:35]([C:38]([O:40][CH3:41])=[O:39])[CH2:36][OH:37])=[O:33])[CH2:28][C:29](=[O:31])[NH2:30])=[O:25])[C@@H:21]([CH3:23])[OH:22])=[O:18])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:49])[C@H:44]([CH2:46][CH3:47])[CH3:45]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 333451Boc-Ile-OSuHCID 131715375HCID 131715375, compound

Product 1

HCID 131714602HCID 131714602, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution cooled on an ice bath of 5.14 g of TFA, H-Phe-Thr-Asn-Ser-OMe (8.78 mM) in 100 ml of DMF has 3.17 g of Boc-Ile-OSu (9.66 mM), 1.30 g of HOBt (9.62 mM) and N-ethyl morpholine added thereto until a pH of 7 is obtained. After 20 hours of reaction at ambient temperature, the solution is concentrated under reduced pressure and the residue taken up in ether gives a precipitate which is filtered and dried in vacuo. 5.24 g of product are obtained.

Workup

  1. additionadded
  2. customuntil a pH of 7 is obtained
  3. customAfter 20 hours of reaction at ambient temperature
  4. concentrationthe solution is concentrated under reduced pressure
  5. customgives a precipitate which
  6. filtrationis filtered
  7. customdried in vacuo

Sources & evidence

ORD record
ord-5850ef88d8d643fca8d30ea822469bf2
Source dataset
uspto-grants-1987_11
Patent number
US04704450

Reaction notes

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