1,3-Thiazole-5-carbaldehyde → HCID 66875151, compound

HRID 1799640Notes

Reaction equation

HRID 1799640 reaction equation
[S:1]1[C:5]([CH:6]=O)=[CH:4][N:3]=[CH:2]1.[Br-].C(CCCCCCCC[P+]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(C1C=CC=CC=1)C1C=CC=CC=1)(O)=O.S1C(C=CCCCCCCCC(O)=O)=CN=C1.S1C(C=CCCCCCCCC(Cl)=O)=CN=C1.Cl.Cl.C(OC(=O)C[C@@H](N)CN(C)C)C1C=CC=CC=1.[CH2:92]([O:99][C:100](=[O:127])[CH2:101][C@@H:102]([NH:107][C:108](=[O:126])[CH2:109][CH2:110][CH2:111][CH2:112][CH2:113][CH2:114][CH2:115][CH:116]=CC1C=CC=C(F)C=1F)[CH2:103][N:104]([CH3:106])[CH3:105])C1C=CC=CC=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>>[CH2:92]([O:99][C:100](=[O:127])[CH2:101][CH:102]([NH:107][C:108](=[O:126])[CH2:109][CH2:110][CH2:111][CH2:112][CH2:113][CH2:114][CH2:115][CH2:116][CH2:6][C:5]1[S:1][CH:2]=[N:3][CH:4]=1)[CH2:103][N:104]([CH3:105])[CH3:106])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

8

Reactant 7

HCID 27735771,3-Thiazole-5-carbaldehydeHCID 10918084Phosphonium, (8-carboxyoctyl)triphenyl-, bromideHCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 66875146HCID 66875146, compound2×HCID 66875223HCID 66875223, compoundHCID 86635495HCID 86635495, compoundHCID 131722655TFA triethylsilane

Product 1

HCID 66875151HCID 66875151, compound

Procedure

The title compound, m/e=384.3 ([M+H]+), was produced in analogy with example 43, steps 1 to 4. Thus, thiazole-5-carboxaldehyde was reacted in step 1 with (8-carboxy-octyl)-triphenyl-phosphonium bromide, leading to 10-(thiazol-5-yl)-dec-9-enoic acid. In step 2, this was converted to 10-(thiazol-5-yl)-dec-9-enoyl chloride, then reacted with (R)-3-amino-4-dimethylamino-butyric acid benzyl ester dihydrochloride, leading to (R)-4-dimethylamino-3-[10-(2,3-difluoro-phenyl)-dec-9-enoylamino]-butyric acid benzyl ester. In step 3, reaction of (R)-4-dimethylamino-3-[10-(2,3-difluoro-phenyl)-dec-9-enoylamino]-butyric acid benzyl ester with triethylsilane-trifluoroacetic acid produced 4-dimethylamino-3-(10-thiazol-5-yl-decanoylamino)-butyric acid benzyl ester, which was hydrolyzed in step 4.

Sources & evidence

ORD record
ord-905a8b30254143b8aa908c3fb81a6ef8
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

Loading…