Hydrochloric Acid → HCID 15280901, compound

HRID 2269591Notes

Reaction equation

[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([OH:5])=O.Cl.[NH:14]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH3:15].CCN(CC)CC.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([N:14]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH3:15])=[O:5]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of Boc-Gly-OH (2.70 g, 15.4 mmol) and the HCl salt of H2N-Sar-OMe (2.15 g, 15.4 mmol) in CH2Cl2 (50 mL) was treated sequentially with Et3N (2.2 mL, 15.8 mmol), DCC (3.20 g, 15.5 mmol), and DMAP (306 mg, 2.5 mmol) and the reaction mixture was stirred at 25° C. for 20 h. A white precipitate formed in the first 10 min and was removed by filtration at the end of the reaction. The filtrate was concentrated in vacuo. Flash chromatography (SiO2, 5×16 cm, 40% EtOAc-hexane eluent) afforded 200 (3.21 g, 4.01 g, theoretical, 80%) as a colorless oil which solidified on standing: mp 72-73° C. (EtOAc-hexane, colorless cubes); Rf=0.32 (50% EtOAc-hexane); 1H NMR (CDCl3, 400 MHz) 4:1 mixture of two conformers, for the major conformer: 5.44 (s, 1H), 4.14 (s, 2H), 4.02 (d, 2H, J=4.3 Hz), 3.73 (s, 3H), 3.02 (s, 3H), 1.43 (s, 9H); 13C NMR (CDCl3, 100 MHz) for major conformer: 169.3, 168.7, 155.7, 79.6, 52.2, 49.4, 42.2, 35.2, 28.3; IR (KBr)max 3419, 2978, 2934, 1754, 1715, 1667, 1488, 1424, 1367, 1249, 1208, 1175, 1120, 1051, 952, 871, 764, 712 cm−1; FABHRMS (NBA-NaI) m/z 283.1259 (M+Na+, C11H20N2O5 requires 283.1270).

Workup

customA white precipitate formed in the first 10 min
customwas removed by filtration at the end of the reaction
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-b30e114c015e4605be1ac6affe9ff8fe
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329497B1

Reaction notes

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