Trifluoroacetic acid → HCID 131711784, compound

HRID 1706296Notes

Reaction equation

HRID 1706296 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][C@H:18]([C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[C@@H:19]([CH3:21])[OH:20])=[O:16])[CH2:11][C:12](=[O:14])[NH2:13])=[O:8])[CH2:3][CH2:4][CH2:5][CH3:6].C(O)(C(F)(F)F)=O.[NH:46]([C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[C@H:47]([C:52]([OH:54])=O)[CH2:48][CH:49]([CH3:51])[CH3:50].C1C2C3C(=O)N(O)C(=O)C3C1C=C2.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[NH:46]([C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[C@H:47]([C:52]([NH:1][C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][C@H:18]([C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])[C@@H:19]([CH3:21])[OH:20])=[O:16])[CH2:11][C:12](=[O:14])[NH2:13])=[O:8])[CH2:3][CH2:4][CH2:5][CH3:6])=[O:54])[CH2:48][CH:49]([CH3:50])[CH3:51]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneHCID 131711782HCID 131711782, compound

Product 1

HCID 131711784HCID 131711784, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Boc-Nle-Asn-Thr-OBzl (3.50 g) was treated with TFA (30 ml) and the solvent was evaporated. The residue was triturated with ether to give powders, which were dissolved in DMF (30 ml) together with TEA (1.2 ml). To this was added Boc-Leu-ONB which was prepared from Boc-Leu-OH (1.66 g), HONB (1.41 g) and DCC (1.63 g). The mixture was stirred at room temperature for 15 hours and the solvent was evaporated. The residue was triturated with water (50 ml) to give powders, which were collected by filtration and washed with ethyl acetate. Yield 3.60 g (83.8%); m.p. 200°-201° C. [α]D21.5 -22.7° (c=0.8, DMF), Rf1 0.60

Workup

  1. customthe solvent was evaporated
  2. customThe residue was triturated with ether
  3. customto give powders, which
  4. customthe solvent was evaporated
  5. customThe residue was triturated with water (50 ml)
  6. customto give powders, which
  7. filtrationwere collected by filtration
  8. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-5651d9d0f107447996c97735724134de
Source dataset
uspto-grants-1980_06
Patent number
US04206199

Reaction notes

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