Sodium hydride → N-Benzyloxycarbonyl-3(R,S)-[(2-carbamoyl)ethen-1-yl]-1,2,3,4-tetrahydroquinoline

HRID 863328Notes

Reaction equation

C(OC([N:11]1C2C=CC=CC=2OC(C=O)C1)=O)C1C=CC=CC=1.C[Si](C(P(OCC)(OCC)=O)C([O-])=O)(C)C.[H-].[Na+].[CH2:41]([O:48][C:49]([N:51]1[C:60]2[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=2)[CH2:54][CH:53]([CH:61]=[CH:62][C:63]([OH:65])=O)[CH2:52]1)=[O:50])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>>[CH2:41]([O:48][C:49]([N:51]1[C:60]2[C:55](=[CH:56][CH:57]=[CH:58][CH:59]=2)[CH2:54][CH:53]([CH:61]=[CH:62][C:63](=[O:65])[NH2:11])[CH2:52]1)=[O:50])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

Reactant 4

HCID 24758Sodium hydride

HCID 19697651N-benzyloxycarbonyl-2(R,S)-formyl-3,4-dihydro-2H-1,4-benzoxazine

HCID 77174746Trimethylsilyidiethylphosphonoacetate

HCID 77325549N-benzyloxycarbonyl-3(R,S)-[(2-carboxy)ethen-1-yl]-1,2,3,4-tetrahydroquinoline

Product 1

HCID 77325273N-Benzyloxycarbonyl-3(R,S)-[(2-carbamoyl)ethen-1-yl]-1,2,3,4-tetrahydroquinoline

Procedure

The reaction of 1.48 g of N-benzyloxycarbonyl-2(R,S)-formyl-3,4-dihydro-2H-1,4-benzoxazine (Example 107) with 2.15 ml of trimethylsilyl-diethylphosphonoacetate and 0.3 g of sodium hydride (80% dispersion in oil) gives, after customary working up, 1.7 g of N-benzyloxycarbonyl-3(R,S)-[(2-carboxy)ethen-1-yl]-1,2,3,4-tetrahydroquinoline. The title compound is obtained therefrom in a manner analogous to that described in Example 1a): Rf (X)=0.47.

Workup

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Sources & evidence

ORD record: ord-48944f0f5ed24937ac5cec828f93d2ba
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05719141

Reaction notes

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