1-Hydroxybenzotriazole → Boc-Glu(OtBu)-Ser(tBu)-Asn-Gly

HRID 2407054Notes

Reaction equation

C1C=CC2N([OH:10])N=NC=2C=1.[NH:11]1CCC[CH2:13][CH2:12]1.C[N:18]([CH:20]=[O:21])[CH3:19].[NH:22]([C:31](OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=[O:32])[C@H:23]([C:28]([OH:30])=[O:29])CC(=O)N.[NH:48]([C:59]([O:61]CC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:49](C(O)=O)[CH2:50][O:51][C:52]([CH3:55])([CH3:54])[CH3:53].[NH:76]([C:90]([O:92][C:93]([CH3:96])([CH3:95])[CH3:94])=[O:91])[C@H:77](C(O)=O)[CH2:78][CH2:79][C:80](=[O:86])[O:81][C:82]([CH3:85])([CH3:84])[CH3:83]>CN(C=O)C>[NH:76]([C:90]([O:92][C:93]([CH3:94])([CH3:95])[CH3:96])=[O:91])[C@H:77]([C:59]([NH:48][C@H:49]([C:20]([NH:18][C@H:19]([C:31]([NH:22][CH2:23][C:28]([OH:30])=[O:29])=[O:32])[CH2:13][C:12](=[O:10])[NH2:11])=[O:21])[CH2:50][O:51][C:52]([CH3:53])([CH3:54])[CH3:55])=[O:61])[CH2:78][CH2:79][C:80](=[O:86])[O:81][C:82]([CH3:83])([CH3:84])[CH3:85]

Participants

Conditions

Temperature: 25 °C

Procedure

An amino acid whose amino group had been protected, HOBt (67.6 mg, 0.50 mmol), and DIPCI (77.0 μL, 63.1 mg, 0.50 mmol) were dissolved in DMF (2 mL), and the obtained solution was then activated for 15 minutes. Thereafter, the solution was placed in the solid-phase synthesis column. After stirring at 25° C. for 1 hour, the Fmoc group was treated with a 20% piperidine/DMF solution (2 mL) for 20 minutes for deprotection. These operations were repeated, so that amino acids were successively condensed. As the protected amino acids, Fmoc-Asn (177.2 mg, 0.50 mmol), Fmoc-Ser(tBu) (191.6 mg, 0.50 mmol), and Boc-Glu(OtBu) (151.6 mg, 0.50 mmol) were used. On the solid-phase resin, a 4-residue peptide having a protecting group, Boc-Glu(OtBu)-Ser(tBu)-Asn-Gly (SEQ ID NO: 33), was obtained.

Workup

customThereafter, the solution was placed in the solid-phase synthesis column
customcondensed

Sources & evidence

ORD record: ord-3d20b491acde4ba49a4f3deaecaa6d6b
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809258B2

Reaction notes

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