Benzyl Alcohol → HCID 20193448, compound

HRID 2118884Notes

Reaction equation

HRID 2118884 reaction equation
[NH2:1][CH:2]1[CH2:8][CH2:7][CH2:6][CH:5]([CH3:9])[N:4]([CH2:10][O:11][C:12]([CH3:15])(C)C)[C:3]1=[O:16].C(O)[C:18]1[CH:23]=[CH:22]C=[CH:20][CH:19]=1.S(Cl)([Cl:27])=O>>[ClH:27].[NH2:1][CH:2]1[CH2:8][CH2:7][CH2:6][CH:5]([CH3:9])[N:4]([CH2:10][O:11][CH2:12][C:15]2[CH:22]=[CH:23][CH:18]=[CH:19][CH:20]=2)[C:3]1=[O:16]

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 24386Thionyl ChlorideHCID 20193495HCID 20193495, compound

Product 1

HCID 20193448HCID 20193448, compound

Procedure

Reaction of the major isomer of 3-amino-1-t-butoxymethyl-7-methylperhydroazepin-2-one with benzyl alcohol and thionyl chloride yields 3-amino-1-benzyloxymethyl-7-methylperhydroazepin-2-one hydrochloride, which after treatment with base, yields the free amino ester. Reaction of this amino ester as described in Example 37 affords the products of Formula I (R3, R5, R6 =H; CH3 ; R=OH) listed in Table IV.

Sources & evidence

ORD record
ord-837eb5c885a440389c936b75cabc05ae
Source dataset
uspto-grants-1987_07
Patent number
US04680392

Reaction notes

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