Triethylamine → HCID 73294499, compound

HRID 530465Notes

Reaction equation

CCN(CC)CC.O[C@@H:9]([CH3:23])[C@@H:10]([NH:14][C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:16])[C:11]([OH:13])=[O:12].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH2:18]([O:17][C:15](=[O:16])[NH:14][C@H:10]1[C:11](=[O:13])[O:12][C@H:9]1[CH3:23])[CH2:19][CH2:20][CH2:21][CH3:22]

Participants

Conditions

Temperature: 0 °C

Procedure

In a four necked round bottom flask, Et3N (3.75 mL, 26.9 mmol) was added to a solution of (2R,3S)-3-hydroxy-2-{[(pentyloxy)carbonyl]amino}butanoic acid (2 g, 8.96 mmol) in dry CH2Cl2 (100 mL) under argon. After cooling at 0° C., PyBOP (6.1 g, 11.6 mmol) was added and the mixture stirred 3 h at 0° C., then 3.5 h at rt. The solvent was removed under vacuum and crude purified by typical silica gel column chromatography, eluting with Cy/AcOEt (from 95:5 to 60:40). The resulting white solid (0.539 g) was further triturated with cyclohexane, yielding a pure compound (0.434 g, 22.5%) as white solid. MS (ESI) m/z: 214.21 [M−H]−. FTIR (cm−1): 3323, 3074, 2958, 2931, 2871, 1854, 1692, 1545, 1471, 1391, 1334, 1270, 1150, 1126, 1087, 1025, 982, 844, 823. 1H NMR (CDCl3): δ 0.91 (t, 3H); 1.31-1.35 (m, 4H); 1.47 (d, 3H); 1.60-1.67 (m, 2H); 4.06-4.14 (m, 2H); 4.84-4.91 (m, 1H); 5.42-5.49 (m, 2H).

Workup

custom3.5 h
customat rt
customThe solvent was removed under vacuum and crude
custompurified by typical silica gel column chromatography
washeluting with Cy/AcOEt (from 95:5 to 60:40)
customThe resulting white solid (0.539 g) was further triturated with cyclohexane

Sources & evidence

ORD record: ord-24980e522239453a85da4da80c709870
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353075B2

Reaction notes

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