Triethylamine → HCID 178501735, compound

HRID 482940Notes

Reaction equation

HRID 482940 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:12]/[O:13][C:14]([C:17]([OH:19])=O)([CH3:16])[CH3:15])/[C:8]([O:10][CH3:11])=[O:9])[N:6]=1.C(N(CC)C(C)C)(C)C.C1(OP(Cl)(OC2C=CC=CC=2)=O)C=CC=CC=1.[C:46]([N:65]1[CH2:70][CH2:69][NH:68][CH2:67][CH2:66]1)([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.C(N(CC)CC)C>CN(C)C=O.O1CCCC1>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:12]/[O:13][C:14]([CH3:15])([CH3:16])[C:17](=[O:19])[CH:70]2[CH2:69][NH:68][CH2:67][CH2:66][N:65]2[C:46]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)([C:59]2[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=2)[C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)/[C:8]([O:10][CH3:11])=[O:9])[N:6]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 75654Diphenyl chlorophosphateHCID 81531DiisopropylethylamineHCID 114729311-TritylpiperazineHCID 178501736HCID 178501736, compound

Product 1

HCID 178501735HCID 178501735, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (Z)-2-amino-α-[(1-carboxy-1-methylethoxy)imino]-4-thiazoleacetic acid, methyl ester (3.16 g, 11.0 mmol) in dimethylformamide (44 ml) and N,N-diisopropylethylamine (2.11 ml, 12.1 mmol) at -10° C. was added diphenylchlorophosphate (2.51 ml, 12.1 mmol). After one hour at -10° C., a solution of N-tritylpiperazine (3.87 g, 11.0 mmol correcting for 7% by weight triethylamine) in tetrahydrofuran (20 ml) and triethylamine (1.54 ml, 11.0 mmol) was added over 15 minutes. The reaction was stirred for an additional 15 minutes at -10° C. and for 2 hours at 0° C.

Sources & evidence

ORD record
ord-9be4eecbbb4c4a4ca3fd7b5f6f5237b1
Source dataset
uspto-grants-1986_03
Patent number
US04576749

Reaction notes

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