(1S)-1-phenylpropan-1-amine → HCID 89726564, compound

HRID 926406Notes

Reaction equation

[C:1]1([C@H:7]([NH:10][C:11]([C:13]2[N:21]3[C:16]([O:17][CH2:18][CH2:19][CH2:20]3)=[C:15]([C:22]([NH:24][C@@H:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:26][CH3:27])=[O:23])[CH:14]=2)=[O:12])[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OC(C1NC(Br)=C(C(OCC)=O)C=1)=O)C.C1([C@@H](N)CC)C=CC=CC=1>>[C:1]1([C@@H:7]([NH:10][C:11]([C:13]2[N:21]3[C:16]([O:17][CH2:18][CH2:19][CH2:20]3)=[C:15]([C:22]([NH:24][C@H:25]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:26][CH3:27])=[O:23])[CH:14]=2)=[O:12])[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 3

HCID 6993773(1S)-1-phenylpropan-1-amine

HCID 22179706HCID 22179706, compound

HCID 89726168HCID 89726168, compound

Product 1

HCID 89726564HCID 89726564, compound

Procedure

6.0 mg of 3,4-dihydro-2H-pyrrolo[2,1-b][1,3]oxazine-6,8-dicarboxylic acid bis-[((S)-1-phenyl-propyl)-amide] were prepared in analogy to the preparation of 3,4-dihydro-2H-pyrrolo[2,1-b][1,3]oxazine-6,8-dicarboxylic acid bis-[((R)-1-phenyl-propyl)-amide], starting from 5-bromo-1H-pyrrole-2,4-dicarboxylic acid diethyl ester (354 mg, 1.22 mmol; prepared according to the procedure described in US 2004/0209886), and (S)-1-phenyl-propylamine (284 mg, 2.10 mmol). LC/MS (method 4): Rt=1.31 min; m/z=446.24 (M+H+).

Workup

customprepared

Sources & evidence

ORD record: ord-f8653823feca4a9bb3a3805f91c5af43
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284333B2

Reaction notes

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