Triphenylphosphine → HCID 86759971, compound

HRID 1795073Notes

Reaction equation

[N:1]([C@@H:4]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)[C:5](=[O:11])[N:6]1[CH2:10][CH2:9][S:8][CH2:7]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[NH2:1][C@@H:4]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)[C:5](=[O:11])[N:6]1[CH2:10][CH2:9][S:8][CH2:7]1

Participants

Conditions

Temperature: 60 °C

Procedure

Acid (Example 95, step A. 4.01 g) was converted to tert-butyl 4-[(1S)-1-azido-2-oxo-2-(1,3-thiazolidin-3-yl)ethyl]piperidine-1-carboxylate (1.3 g) in 4 steps using the procedures outlined in Example 6. 1H NMR (500 MHz, CD3OD, HCl salt) δ 4.71–4.49 (m, 2H), 4.09 (bs, 2H), 3.98–3.74 (m, 2H), 3.42 (d, 0.4H, J=7 Hz), 3.40 (d, 0.6H, J=7 Hz), 3.18 (t, 1.2H, J=5.6 Hz), 3.02 (t, 0.8H, J=5.6 Hz), 2.72 (bs, 2H), 2.18 (m, 1H), 1.99 (d, 1H, J=13 Hz), 1.61 (d, 1H, J=13.5 Hz), 1.42 (s, 9H), 1.24 (m, 1H), 1.19 (m, 1H). A portion of this material (30 mg) was dissolved in wet THF and triphenyl phosphine (26 mg) was added to the solution. The mixture was heated at 60° C. for 5 h, cooled, concentrated and purified by preparative TLC on silica gel (eluent: 5 to 10% methanol in CH2Cl2) to give the title compound. 1H NMR (500 MHz, CDCl3) δ 4.68–4.48 (m, 2H), 4.18 (bs, 2H), 3.99–3.69 (m, 2H), 3.36 (d, 0.4H, J=7 Hz), 3.29 (d, 0.6H, J=7 Hz). 3.1 (t, 1.2H, J=5.6 Hz), 3.0 (t, 0.8H, J=5.6 Hz), 2.61 (bs, 2H), 1.92 (bd, 1H, J=13.5 Hz), 1.65 (m, 1H), 1.58 (m, 1H), 1.42 (s, 9H), 1.25 (m, 1H), 1.20 (m, 1H).

Workup

temperaturecooled
concentrationconcentrated
custompurified by preparative TLC on silica gel (eluent: 5 to 10% methanol in CH2Cl2)

Sources & evidence

ORD record: ord-e9e467531e414c328e08065fdcf1969e
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07026316B2

Reaction notes

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