(5-Oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-carbamic acid allyl ester → HCID 22977499, compound

HRID 900582Notes

Reaction equation

HRID 900582 reaction equation
C(O[C:5](=[O:22])[NH:6][CH:7]1[CH2:11][C:10](=[O:12])[O:9][CH:8]1[O:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18]C=1)C=C.[NH2:23][C:24]1[CH:44]=[CH:43][C:27]([C:28]([NH:30][CH:31]([CH3:42])[C:32]([N:34]2[CH2:38][CH2:37][CH2:36][CH:35]2C(O)=O)=[O:33])=[O:29])=[CH:26][C:25]=1[Cl:45].O=C1OC(OCCC2C=CC=CC=2)C(NC(C2CCCN2C(=O)C(NC(=O)C2C=CC(N)=C(Cl)C=2)C)=O)C1>>[CH2:14]([O:13][CH:8]1[CH:7]([NH:6][C:5]([CH:35]2[CH2:36][CH2:37][CH2:38][N:34]2[C:32](=[O:33])[CH:31]([NH:30][C:28](=[O:29])[C:27]2[CH:43]=[CH:44][C:24]([NH2:23])=[C:25]([Cl:45])[CH:26]=2)[CH3:42])=[O:22])[CH2:11][C:10](=[O:12])[O:9]1)[C:15]1[CH:16]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 18465651(5-Oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-carbamic acid allyl esterHCID 186236851-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acidHCID 229775121-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (5-oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-amide

Product 1

HCID 22977499HCID 22977499, compound

Procedure

Was prepared from the syn diastereomer of (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester (40) and 97a following the method used for 98a. The title compound was isolated as a pale yellow solid (720 mg, 51% yield). 1H-NMR (500 MHz, CD3OD) δ 1.16 (d, 0.5H), 1.40 (d, 2.5H), 1.64-2.25 (m, 4H), 2.61 (dd, 1H), 2.79 (dd, 1H), 3.37-3.59 (m, 1H), 3.59-3.74 (m, 1H), 3.77-3.92 (m, 1H), 4.29-4.47 (m, 1H), 4.47-5.02 (m, 4H), 5.48 (s, 0.5H), 5.66 (d, 1H), 5.68 (d, 0.5H), 6.79 (d, 1H), 7.17-7.52 (m, 5H), 7.48-7.62 (m, 1H), 7.68-7.83 (m, 1H). Analytical HPLC 15.98 min. LC-MS (ES+) m/e=529.2 (MH+).

Sources & evidence

ORD record
ord-f3f14983dc7147888a1859146e4e9359
Source dataset
uspto-grants-2008_04
Patent number
US07358273B2

Reaction notes

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