Benzyl Isothiocyanate → HCID 12087612, compound

HRID 430708Notes

Reaction equation

HRID 430708 reaction equation
C(C(C(C([O-])=O)O)O)([O-])=O.[CH2:11]([N:18]=[C:19]=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N=C=S)C1C=CC=CC=1.[CH:31]1([CH2:34][N:35]2[CH2:53][CH2:52][C@:42]34[C:43]5[C:44]6[O:51][C@H:41]3[C@H:40]([NH:54][CH3:55])[CH2:39][CH2:38][C@@:37]4([OH:56])[C@H:36]2[CH2:49][C:48]=5[CH:47]=[CH:46][C:45]=6[OH:50])[CH2:33][CH2:32]1>>[CH:31]1([CH2:34][N:35]2[CH2:53][CH2:52][C@:42]34[C:43]5[C:44]6[O:51][C@H:41]3[C@@H:40]([N:54]([CH3:55])[C:19]([NH:18][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:20])[CH2:39][CH2:38][C@@:37]4([OH:56])[C@H:36]2[CH2:49][C:48]=5[CH:47]=[CH:46][C:45]=6[OH:50])[CH2:32][CH2:33]1

Participants

5

Reactant 4

HCID 2346Benzyl IsothiocyanateHCID 76639Benzyl isocyanateHCID 38061142,3-DihydroxybutanedioateHCID 15908859HCID 15908859, compound

Product 1

HCID 12087612HCID 12087612, compound

Procedure

tartrate 132 (yield: 65%), 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-(N-methyl-N′-benzylthioureido)morphinan.tartrate 133 (yield: 88%) and 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-(N-methyl-N′-benzylthioureido)morphinan.tartrate 134 (yield: 74%) were obtained by following the procedure of example 121 but using benzylisocyanate and benzylisothiocyanate instead of 3,4-dichlorophenylisocyanate, and using 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-methylaminomorphinan 10 instead of 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-methylaminomorphinan 4.

Sources & evidence

ORD record
ord-faa7831762fa401e8ddc41e2c162798b
Source dataset
uspto-grants-2001_11
Patent number
US06323212B1

Reaction notes

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