N-[(pent-4-en-1-yloxy)carbonyl]-norleucine → N-[(but-3-en-1-yloxy)carbonyl]-L-norleucine

HRID 1360098Notes

Reaction equation

HRID 1360098 reaction equation
[CH2:1]([O:6][C:7]([NH:9][C@H:10]([C:15]([OH:17])=[O:16])[CH2:11][CH2:12][CH2:13][CH3:14])=[O:8])[CH2:2][CH2:3][CH:4]=C.C(OC(N[C@H](C(O)=O)CCCC)=O)C=C>>[CH2:1]([O:6][C:7]([NH:9][C@H:10]([C:15]([OH:17])=[O:16])[CH2:11][CH2:12][CH2:13][CH3:14])=[O:8])[CH2:2][CH:3]=[CH2:4]

Participants

3

Reactant 2

HCID 45378373N-[(pent-4-en-1-yloxy)carbonyl]-norleucineHCID 51340333(2S)-2-{[(prop-2-en-1-yloxy)carbonyl]amino}hexanoic acid

Product 1

HCID 57617067N-[(but-3-en-1-yloxy)carbonyl]-L-norleucine

Procedure

The title compound was prepared in a manner similar to Example 1 (Steps 1-8). N-[(but-3-en-1-yloxy)carbonyl]-L-norleucine was prepared according to the procedure used for [(4-pentenyloxy)carbonyl]-L-norleucine (Example 3), and was used in place of N-[(allyloxy)carbonyl]-L-norleucine. 1H NMR (500 MHz, MeOH-d4) ppm: 8.58 (s, 1H), 8.42 (s, 1H), 8.09 (m, 3H), 7.96 (d, 1H), 7.74 (m, 4H), 6.70 (d, J=15.2 Hz, 1H), 6.39 (m, 1H), 5.87 (m, 2H), 5.29 (d, 1H), 5.10 (d, 1H), 4.80 (m, 2H), 4.71 (m, 2H), 4.57 (t, 1H), 4.07 (m, 2H), 2.86 (dd, 1H), 2.70 (m, 1H), 2.55 (m, 1H), 2.48 (t, 1H), 2.17 (dd, 1H), 1.85 (m, 1H), 1.79-1.64 (m, 2H), 1.55-1.37 (m, 5H), 1.01 (t, 3H). LRMS (CI, [M+H]) Calc'd=653.4. found=653.4.

Sources & evidence

ORD record
ord-6ffd468abbb547b1b0eb40ca8793b638
Source dataset
uspto-grants-2011_02
Patent number
US07879797B2

Reaction notes

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