TFA dichloromethane water → HCID 178448278, compound

HRID 847312Notes

Reaction equation

HRID 847312 reaction equation
FC(F)(F)C(O)=O.O.C(Cl)Cl.[C:12]([O:18][CH2:19][CH2:20][C@H:21]([CH:34]([CH3:36])[CH3:35])[CH2:22][C@H:23]([OH:33])[C@@H:24]([NH2:32])[CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14].[NH:37]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[C@H:38]([C:46]([NH:48][C@H:49]([C:56](O)=[O:57])[CH2:50][C:51]1[N:55]=[CH:54][NH:53][CH:52]=1)=[O:47])[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>>[CH:26]1([CH2:25][C@H:24]([NH:32][C:56]([CH:49]([NH:48][C:46]([C@@H:38]([NH:37][C:59](=[O:60])[O:61][C:62]([CH3:64])([CH3:63])[CH3:65])[CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[O:47])[CH2:50][C:51]2[N:55]=[CH:54][NH:53][CH:52]=2)=[O:57])[C@@H:23]([OH:33])[CH2:22][C@@H:21]([CH:34]([CH3:36])[CH3:35])[CH2:20][CH2:19][O:18][C:12](=[O:17])[C:13]([CH3:14])([CH3:16])[CH3:15])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1

Participants

4

Reactant 3

HCID 18672661TFA dichloromethane waterHCID 22845419HCID 22845419, compoundHCID 178454152HCID 178454152, compound

Product 1

HCID 178448278HCID 178448278, compoundYield 37%

Procedure

In an analogous manner to that described in Example 9, 635 mg (1.78 mmol) of t-butyl [(4S,5S)-4-(cyclohexylmethyl)-5-(S)-2-isopropyl-4-(pivaloyloxy)butyl]-2,2-dimethyl-3-oxazolidinecarboxylate are treated with trifluoroacetic acid/water/methylene chloride for the cleavage of the Boc protecting group with simultaneous opening of the oxazolidine ring and the resulting 347 mg (76%) of (3S,5S,6S)-6-amino-7-cyclohexyl-5-hydroxy-3-isopropylheptyl pivaloate are reacted without further purification with Boc-Phe-His-OH, whereby there are obtained 280 mg (37%) of t-butyl [(S)-α-[[(RS)-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-6-(pivaloyloxy)hexyl]carbamoyl]-2-imidazole-4-ylethyl]carbamoyl]phenethyl]carbamate as an amorphous solid, MS: 740 (M+H)+.

Sources & evidence

ORD record
ord-4e26e069444846a5b72cbe68bb3ea7dc
Source dataset
uspto-grants-1992_08
Patent number
US05140011

Reaction notes

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