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

HRID 1360099Notes

Reaction equation

HRID 1360099 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 1-7) and Example 2. N-[(But-3-en-1-yloxy)carbonyl]-L-norleucine was prepared according to the procedure used for [(4-pentenyloxy)carbonyl]-L-norleucine, and was used in place of N-[(allyloxy)carbonyl]-L-norleucine. 1H NMR (500 MHz, MeOH-d4) ppm: 8.59 (s, 1H), 8.34 (s, 1H), 8.10 (m, 3H), 7.96 (d, 1H), 7.77 (m, 4H), 5.82 (m, 2H), 5.30 (d, 1H), 5.10 (d, 1H), 4.82 (m, 2H), 4.64 (m, 2H), 4.59 (t, 1H), 4.10 (m, 2H), 3.80 (m, 1H), 3.08 (m, 1H), 2.88 (m, 2H), 2.60 (m, 1H), 2.19 (dd, 1H), 1.90-1.63 (m, 6H), 1.50-1.40 (m, 5H), 0.95 (t, 3H). LRMS (CI, [M+H]) Calc'd=655.4. found=655.4.

Sources & evidence

ORD record
ord-f7d766a657ad4c4c862e1d3705b3ea8b
Source dataset
uspto-grants-2011_02
Patent number
US07879797B2

Reaction notes

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