Dicyclohexylcarbodiimide → HCID 131711782, compound

HRID 1706295Notes

Reaction equation

HRID 1706295 reaction equation
[NH:1]([C:24]([O:26]C(C)(C)C)=O)[C@H:2]([C:7]([NH:9][C@H:10]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C@@H:11]([CH3:13])[OH:12])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].[NH:31]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[C@H:32](C(O)=O)[CH2:33][CH2:34][CH2:35][CH3:36].C1C2C3C(=O)N(O)C(=O)C3C1C=C2.C1CCC(N=C=NC2CCCCC2)CC1>C(O)(C(F)(F)F)=O.CN(C=O)C>[NH:31]([C:40]([O:42][C:43]([CH3:44])([CH3:46])[CH3:45])=[O:41])[C@H:32]([C:24]([NH:1][C@H:2]([C:7]([NH:9][C@H:10]([C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15])[C@@H:11]([CH3:13])[OH:12])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5])=[O:26])[CH2:33][CH2:34][CH2:35][CH3:36]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneHCID 2733747N-tert-Butoxycarbonyl-L-norleucineHCID 131711783HCID 131711783, compound

Product 1

HCID 131711782HCID 131711782, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Boc-Asn-Thr-OBzl (3.1 g) was dissolved in TFA (30 ml), and the solution was allowed to stand at room temperature for 10 minutes, and the solvent was evaporated. The residue was triturated with ether to give powders, which were dissolved in DMF (30 ml) together with TEA (1.5 ml) and to this was added Boc-Nle-ONB which was prepared from Boc-Nle-OH (1.69 g), HONB (1.50 g) and DCC (1.73 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 ether. Yield 3.8 g (96.7%); m.p. 160°-163° C. [α]D21.5 -13.6° (c=0.8, DMF); Rf1 0.58

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 ether

Sources & evidence

ORD record
ord-f2cc374da3ab4046af39099f7d72128d
Source dataset
uspto-grants-1980_06
Patent number
US04206199

Reaction notes

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