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Triethylamine → Ethyl 5-[2-(tert-butoxycarbonylmethylamino)acetylamino]benzofuran-2-carboxylate

HRID 855780
Notes
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Reaction equation

HRID 855780 reaction equation
[C:1](N(CC(O)=O)C)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:14][C:15]1[CH:16]=[CH:17][C:18]2[O:22][C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:20][C:19]=2[CH:28]=1.CN(C([O:36]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[CH2:61]([N:63]([CH2:66]C)CC)[CH3:62]>CN(C=O)C>[C:4]([O:3][C:1]([CH2:66][NH:63][CH2:61][C:62]([NH:14][C:15]1[CH:16]=[CH:17][C:18]2[O:22][C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:20][C:19]=2[CH:28]=1)=[O:36])=[O:2])([CH3:5])([CH3:6])[CH3:7]
ParticipantsProcedureSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 9837138Ethyl 5-aminobenzofuran-2-carboxylate

Product 1

HCID 69145149
Ethyl 5-[2-(tert-butoxycarbonylmethylamino)acetylamino]benzofuran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 ml of DMF are added to 0.95 g of Boc-sarcosine and 1.21 g of ethyl 5-aminobenzofuran-2-carboxylate. 1.77 g of TBTU and 0.23 g of HOBt are then added, and the mixture is neutralised using 4 ml of triethylamine. The mixture is stirred overnight at room temperature.

Sources & evidence

ORD record
ord-e8643fa016cd4d64a8adc826c5fc6cb3
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07262216B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes