Trifluoroacetic acid → H2N-Pro MBHA resin

HRID 1681988

Reaktionsgleichung

Reaktionsgleichung von HRID 1681988
C(OC([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=O)(C)(C)C.[CH3:16][C:17]1[CH:22]=[CH:21][C:20](C(N)C2C=CC=CC=2)=[CH:19][CH:18]=1.[CH2:31]=[CH:32]C1C=CC=CC=1.[CH2:39]=CC1C=CC(C=C)=CC=1.[ClH:49].N1(C(OC(C)(C)C)=O)CCC[C@H]1C(O)=O.CC1C=CC(C(N)C2C=CC=CC=2)=CC=1.C=CC1C=CC=CC=1.C=CC1C=CC(C=C)=CC=1.Cl.FC(F)(F)C(O)=O>ClCCl.C(N(C(C)C)CC)(C)C.C(N(CC)CC)C>[NH:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11].[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([CH:15]([NH2:8])[C:14]2[CH:13]=[CH:9][CH:10]=[CH:32][CH:31]=2)=[CH:19][CH:18]=1.[CH2:16]=[CH:17][C:10]1[CH:9]=[CH:13][CH:14]=[CH:15][CH:39]=1.[CH2:21]=[CH:22][C:17]1[CH:15]=[CH:14][C:13]([CH:9]=[CH2:10])=[CH:19][CH:18]=1.[ClH:49]

Komponenten

8

Edukt 4

HCID 6422Trifluoroacetic acid2×HCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 71310119MBHA resinHCID 131717703Boc-Pro MBHA resin

Produkt 1

HCID 131717702H2N-Pro MBHA resin

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittel3×HCID 8471TriethylamineLösungsmittelHCID 81531DiisopropylethylamineLösungsmittel

Versuchsvorschrift

Peptides described in this invention are prepared starting from t-butyloxycarbonyl-proline linked to MBHA resin (Boc-Pro-MBHA) which is also commercially available. Boc-Pro-MBHA resin is treated with anhydrous trifluoroacetic acid (TFA) or 25% to 75% mixture of TFA in dichloromethane (TFA-DCM) to deprotect the amino group, and the resulting salt neutralized using 5% to 20% triethylamine in DCM (TEA-DCM) or 5% to 20% diisoproylethylamine in DCM (DIEA-DCM) to furnish H2N-Pro-MBHA resin.

Aufarbeitung

  1. customare prepared

Quellen und Nachweise

ORD-Eintrag
ord-6e90bb00ca8f4d9882e5a721f2d63280
Quelldatensatz
uspto-grants-1992_12
Patentnummer
US05175146

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