1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Boc-Gly-Gly-Val-Pro-OBzl

HRID 1086786Notes

Reaction equation

HRID 1086786 reaction equation
N(C(OC(C)(C)C)=O)CC(N[C@H](C(N[CH2:13][C:14]([NH:16][C@H:17]([C:22]([N:24]1[CH2:38][CH2:37][CH2:36][C@H:25]1[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])=[O:23])[C@H:18]([CH2:20]C)[CH3:19])=[O:15])=O)C(C)C)=O.Cl.O1CCOCC1.[NH:53]([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[CH2:54][C:55]([NH:57]CC(O)=O)=[O:56].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[NH:53]([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[CH2:54][C:55]([NH:57][CH2:13][C:14]([NH:16][C@H:17]([C:22]([N:24]1[CH2:38][CH2:37][CH2:36][C@H:25]1[C:26]([O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:27])=[O:23])[CH:18]([CH3:19])[CH3:20])=[O:15])=[O:56]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 3334662-(2-{[(Tert-butoxy)carbonyl]amino}acetamido)acetic acidHCID 204431481,4-Dioxane hydrochlorideHCID 131715771Boc-Gly-Val-Gly-Ile-Pro-OBzl

Product 1

HCID 14306249Boc-Gly-Gly-Val-Pro-OBzl

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

III (6.0 g, 0.0148 mole) (39) was deblocked with HCl/Dioxane and solvent removed under reduced pressure. The residue was triturated with ether, filtered, washed with ether, then pet. ether and dried. A very hygroscopic material was obtained (4.2 g, 0.0123 mole) which was coupled in DMF with II (2.86 g, 0.0123 mole) in the presence of 10% excess of EDCI (2.60 g) and HOBt (2.07 g). The reaction was worked up as described for I to obtain IV as a white foam in a quantitative yield, no sharp m.p. 54°-62° C. Rf2, 0.42; Rf3, 0.74. Anal. Calcd. for C26H38N4O7 ; C, 60.21; H, 7.38; N, 10.80%. Found: C, 60.0; H, 7.46; N, 10.81%.

Workup

  1. customremoved under reduced pressure
  2. customThe residue was triturated with ether
  3. filtrationfiltered
  4. washwashed with ether
  5. dry with materialpet. ether and dried
  6. customA very hygroscopic material was obtained (4.2 g, 0.0123 mole) which

Sources & evidence

ORD record
ord-d53a8c178d654f689031c79ba1946bff
Source dataset
uspto-grants-1991_07
Patent number
US05032271

Reaction notes

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