Triethylamine → Dicyclohexylcarbodiimide

HRID 1755804Notes

Reaction equation

HRID 1755804 reaction equation
COC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)C(N1CCC(C(NC(=O)[C@H](C)N)C)=CC(C[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)C1)C.[O:43](C(=O)[C@H](C[C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1)NC(OC(C)(C)C)=O)[C:44](=[O:61])[C@H:45]([CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[NH:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48].COC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)C(N1CCC(C([NH:100][C:101](OC(C)(C)C)=O)C)=CC(CC2C=CC=CC=2)C1)C.CC[N:126](CC)CC>CN(C=O)C>[C:47]([NH:46][C@H:45]([C:44]([OH:61])=[O:43])[CH2:54][C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)([O:49][C:50]([CH3:52])([CH3:51])[CH3:53])=[O:48].[CH2:76]1[CH2:75][CH2:74][CH:73]([N:126]=[C:101]=[N:100][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]2)[CH2:78][CH2:77]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9960061HCID 9960061, compoundHCID 10791872HCID 10791872, compound2×HCID 70086251HCID 70086251, compound

Product 2

HCID 10868DicyclohexylcarbodiimideHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared in a manner similar to compound (15) in Example 2 using (Boc-Phe)2O instead of (Boc-Ala)2O. To the di-hydrochloride of compound (14) (100 mg), prepared as in Example 2, in DMF (5 mL) was added NEt3 (47 uL) followed by (Boc-Phe)2O, obtained from Boc-phenylalanine (0.18 g) and DCC (0.07 g). The reaction was stirred for 16 h at room temperature and evaporated to dryness. Flash chromatography on silica gel eluted with 60% EtOAc in n-hexane afforded the product as a mixture of isomers. TLC Rf 0.35 (silica, 60% EtOAc, n-hexane).

Sources & evidence

ORD record
ord-57f8449d1c874dbdb6cec03b54b7d535
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

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