1-t-Butyloxycarbonyl-4-((2-carboxymethoxyphenyl)amino)piperidine → 4-(3-Oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1377681Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:22][C:23](O)=[O:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH2:22][C:23]2=[O:24])[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

Reactant 2

HCID 223807041-t-Butyloxycarbonyl-4-((2-carboxymethoxyphenyl)amino)piperidine

HCID 86583742Edc hobt

Product 1

HCID 223806764-(3-Oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-piperidine-1-carboxylic acid tert-butyl ester

Procedure

1-t-Butyloxycarbonyl-4-((2-carboxymethoxyphenyl)amino)piperidine (5.2 g, 15 mmol) from Step 3 was cyclized using the EDC/HOBT coupling procedure given in Step 5 of Example 1. 4-(1-tert-butyloxycarbonyl-4-piperidinyl)-(2H)-1,4-benzoxazin-3(4H)-one was obtained as a foam (86% yield).

Sources & evidence

ORD record: ord-dc198efe4a6d42609857a4d46bc344ad
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05665719

Reaction notes

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