Benzyl Bromide → HCID 11333520, compound

HRID 1802972Notes

Reaction equation

C(O)CCCCCCCO.C(Br)C1C=CC=CC=1.C(OCCCCCCCCO)C1C=CC=CC=1.C(OCCCCCCCC(O)=O)C1C=CC=CC=1.Cl.Cl.[CH2:56]([O:63][C:64](=[O:72])[CH2:65][C@@H:66](N)[CH2:67][N:68]([CH3:70])[CH3:69])[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>>[CH2:56]([O:63][C:64](=[O:72])[CH2:65][CH2:66][CH2:67][N:68]([CH3:69])[CH3:70])[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1

Participants

Reactant 5

HCID 7498Benzyl Bromide

HCID 694201,8-Octanediol

HCID 11481775HCID 11481775, compound

HCID 18795073HCID 18795073, compound

HCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochloride

Product 1

HCID 11333520HCID 11333520, compound

Procedure

The title compound, m/e=377.6 ([M−H]−), was produced in analogy with intermediate 1, steps 1 to 4. Thus, 1,8-octanediol was alkylated in step 1 with benzyl bromide, leading to 8-benzyloxy-octan-1-ol, which was oxidized in step 2 to 8-benzyloxy-octanoic acid. This was coupled in step 3 with (R)-3-amino-4-dimethylamino-butyric acid benzyl ester dihydrochloride to produce (R)-3-[8-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record: ord-54b82b90adc34b798c26c5d46c057423
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349893B2

Reaction notes

Loading…