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Dimethylformamide → 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

HRID 623275
Notes
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Reaction equation

HRID 623275 reaction equation
[CH3:1][N:2]([CH:4]=[O:5])[CH3:3].[NH:6]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[C@H:7]([C:17]([NH:19][C@H:20]([C:36](OCC1C=CC=CC=1)=O)CC1C=CC(OCC2C=CC=CC=2)=CC=1)=O)[CH2:8][O:9]CC1C=CC=CC=1.CS(O)(=O)=[O:55].C1C=C[C:61]2N(O)N=[N:64][C:62]=2C=1>O.CCN(CC)CC>[NH:6]([C:46]([O:48][C:49]([CH3:50])([CH3:51])[CH3:52])=[O:47])[C@H:7]([C:8]([OH:9])=[O:55])[CH2:17][C:4](=[O:5])[NH2:2].[CH3:61][CH2:62][N:64]=[C:17]=[N:19][CH2:20][CH2:36][CH2:4][N:2]([CH3:3])[CH3:1]
ParticipantsProcedureSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 6395Methanesulfonic AcidHCID 757711-HydroxybenzotriazoleHCID 14012223Boc-Ser(Bzl)-Tyr(Bzl)-OBzl

Product 2

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 82035N2-((tert-Butoxy)carbonyl)-L-asparagine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

[α]D20 =-16.7° (C=1, DMF) (B) From 133.2 g of DP-2, 100 g of methansulfonic acid, 84.4 g of Et3N, 36.7 g of HOBt.H2O, 55.7 g of Boc-Asn-OH and 37.2 g of WSC, 157 g (100%) of DP-3 are obtained by employing the same technique described in example I-7.

Sources & evidence

ORD record
ord-3cec2931050a4df88a6f2bd44591a367
Source dataset
uspto-grants-1988_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04774319

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes