Propanal → 2-[5-Benzyl-3,6-dioxo-1-propyl-(2S, 5S)-perhydro-2-pyrazinyl]acetic acid

HRID 399096Notes

Reaction equation

HRID 399096 reaction equation
[NH:1]([C:14](OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:2](C(O)=O)[CH2:3][C:4](=[O:10])[O:5]C(C)(C)C.[CH:31](=O)[CH2:32]C.[NH:35]([C:47]([O:49]C(C)(C)C)=O)[C@H:36]([C:44]([OH:46])=O)[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C1C=NC2N(O)N=NC=2C=1.CC(C)N=C=NC(C)C>CC(O)=O.C1(C)C=CC=CC=1.O>[CH2:37]([C@H:36]1[C:44](=[O:46])[N:1]([CH2:14][CH2:31][CH3:32])[C@@H:2]([CH2:3][C:4]([OH:5])=[O:10])[C:47](=[O:49])[NH:35]1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

7

Reactant 4

HCID 527PropanalHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 2724635Fmoc-L-Asp(OtBu)-OHHCID 131720865HOAt DIC

Product 1

HCID 1017058812-[5-Benzyl-3,6-dioxo-1-propyl-(2S, 5S)-perhydro-2-pyrazinyl]acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 18331056Acetic acid tolueneSolvent

Procedure

Hydroxymethyl PAM resin was coupled with FmocAsp(OtBu)-OH (Mukaiyama conditions) and reductively alkylated with propionaldehyde. BocPhe was coupled with HOAt/DIC and after Boc-deprotection the DKP formed in 1% HOAc/toluene (12 h). Yield: 45 mg (22%). 1H-NMR (400 MHz, CDCl3):δ=0.89 (t,J=7.3 Hz, 3 H), 1.45-1.49 (m,1 H), 1.65-1.69 (m, 1 H), 1.92 (dd, J=6.5, 16.7 Hz, 1 H), 2.10 (dd, J=3.6, 16.7 Hz, 1 H), 2.86-2.93 (m, 1 H), 3.11 (dd, J=3.6, 13.5 Hz, 1 H), 3.24 (dd, J=6.4, 13.5 Hz, 1 H), 3.59-3.67 (m, 1 H), 4.25 (m, 1 H), 4.36 (m, 1 H), 5.41 (broad s, 1 H), 7.16-7.18 (m, 2 H), 7.30-7.34 (m, 2 H), 7.50-7.54 (m, 1 H). 13 C-NMR (101 MHz, CDCl3):δ=11.1, 19.9, 36.9, 40.3, 46.6, 55.8, 56.5, 127.7, 128.9, 130.2, 134.9, 164.9, 168.3, 173.5. Anal. Calcd. for C16H20N2O4.1.5 H2O:C,57.99; H, 7.00; N, 8.45, found: C, 57.45; H,6.35; N, 8.91

Sources & evidence

ORD record
ord-030d0c7817d64528ba0f8b6ddd1865c0
Source dataset
uspto-grants-1998_10
Patent number
US05817751

Reaction notes

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