Potassium Iodide → (R)-3-(tert-Butoxycarbonylamino)-5-(p-isopropylbenzyl)-2,3,4,5-tetrahydro-1,5-benzoxazepin-4-one

HRID 975809Notes

Reaction equation

HRID 975809 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C:15](=[O:16])[NH:14][C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[O:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N[C@@H]1C(=O)NC2C=CC=CC=2OC1)=O)(C)(C)C.C(N[C@@H](C(O)=O)CO)(OC(C)(C)C)=O.[CH:55]([C:58]1[CH:65]=[CH:64][C:61]([CH2:62]Cl)=[CH:60][CH:59]=1)([CH3:57])[CH3:56].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CCCCCC.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]1[C:15](=[O:16])[N:14]([CH2:62][C:61]2[CH:64]=[CH:65][C:58]([CH:55]([CH3:57])[CH3:56])=[CH:59][CH:60]=2)[C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[O:11][CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 6

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 749164-Isopropylbenzyl chlorideHCID 637603(R)-2-tert-butoxycarbonylamino-3-hydroxy propionic acidHCID 18599719(S)-tert-Butyl (4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)carbamateHCID 54323944tert-Butyl (R)-(4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)carbamate

Product 1

HCID 54070159(R)-3-(tert-Butoxycarbonylamino)-5-(p-isopropylbenzyl)-2,3,4,5-tetrahydro-1,5-benzoxazepin-4-one

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Obtained analogously to the directions in Example 1a) starting from 4.8 g of (R)-3-(tert-butoxycarbonyl-amino)-2,3-dihydro-1,5-benzoxazepin-4-one (prepared analogously to (S)-3-(tert-butoxycarbonylamino)-2,3-dihydro-1,5-benzoxazepin-4-one, starting from N-Boc-(D)-serine), 4.4 g of p-isopropylbenzyl chloride, 2.9 g of potassium carbonate and 166 mg of potassium iodide. Rf value (eluant: hexane/ethyl acetate 4:1): 0.33.

Workup

  1. customObtained analogously to the directions in Example 1a)

Sources & evidence

ORD record
ord-741de2c07a5f452484f69758833f102d
Source dataset
uspto-grants-1997_03
Patent number
US05610153

Reaction notes

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