Triethylamine → HCID 87090959, compound

HRID 417759Notes

Reaction equation

[NH2:1][CH:2]([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].C(N(CC)CC)C.FC1C(F)=C(F)C(F)=C([O:22][C:23]([CH2:25][CH2:26][CH2:27][CH2:28][C@H:29]2[C@@H:37]3[C@@H:32]([NH:33][C:34]([NH:36]3)=[O:35])[CH2:31][S:30]2)=O)C=1>CN(C=O)C>[C:23]([NH:1][CH:2]([CH3:7])[CH2:3][C:4]([OH:6])=[O:5])(=[O:22])[CH2:25][CH2:26][CH2:27][CH2:28][C@H:29]1[C@@H:37]2[C@@H:32]([NH:33][C:34]([NH:36]2)=[O:35])[CH2:31][S:30]1

Participants

Conditions

Temperature: 25 °C

Procedure

Preparation was accomplished as described by Wilbur [Bioconj. Chem. 1997, 8, 572]. To a 0.13 g (1.3 mmol) quantity of 3-aminobutyric acid dissolved in 20 mL of DMF under argon atmosphere was added 0.4 mL (2.5 mmol) of triethylamine followed by 0.5 g (1.3 mmol) of biotin tetrafluorophenyl ester. The reaction was stirred at 25° C. for 24 h and the solvent was removed under vacuum. The residue was triturated with acetonitrile and filtered. The isolated solid was dried under vacuum to yield 0.5 g (98%) of product as a colorless solid, mp 161-163° C. 1H NMR (DMSO-d6): O 7.6 (m, 1H), 6.2 (d, J=11.2 Hz, 2H), 3.9-4.2 (m, 3H), 2.6 (m, 2H), 2.35 (d, J=12.6 Hz, 1H), 1.7-2.1 (m, 4H), 0.7-1.5 (m, 10H).

Workup

customPreparation
customthe solvent was removed under vacuum
customThe residue was triturated with acetonitrile
filtrationfiltered
customThe isolated solid was dried under vacuum

Sources & evidence

ORD record: ord-5e7a11f46e2c4c7983ef69aa021968b7
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08092782B2

Reaction notes

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