Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 178455992, compound

HRID 1655749Notes

Reaction equation

HRID 1655749 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH:9][C:10]([CH2:12][CH:13]([CH2:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[C:14]([OH:16])=O)=[O:11])[CH2:3][CH2:2]1.[NH2:28][C@@H:29]([CH2:50][C:51]1[N:52]=[CH:53][NH:54][CH:55]=1)[C:30]([NH:32][C@@H:33]([CH2:43][CH:44]1[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]1)[C@@H:34]([OH:42])[CH2:35][C@@H:36]([CH:39]([CH3:41])[CH3:40])[CH:37]=[CH2:38])=[O:31].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C>[CH:44]1([CH2:43][C@H:33]([NH:32][C:30](=[O:31])[CH:29]([NH:28][C:14](=[O:16])[CH:13]([CH2:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[CH2:12][C:10](=[O:11])[NH:9][CH2:8][CH2:7][N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)[CH2:50][C:51]2[N:52]=[CH:53][NH:54][CH:55]=2)[C@@H:34]([OH:42])[CH2:35][C@@H:36]([CH:39]([CH3:41])[CH3:40])[CH:37]=[CH2:38])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49]1

Participants

5

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 19791010HCID 19791010, compoundHCID 178456019HCID 178456019, compound

Product 1

HCID 178455992HCID 178455992, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 95 mg of (RS)-α-[(2-morpholinoethyl)carbamoylmethyl]-1-naphthalenepropionic acid, 100 mg of (S)-α-amino-N-[(1S,2S.4S)-1-(cyclohexylmethyl) 2-hydroxy-4-isopropyl-5-hexenyl]imidazole-4-propionamide and 97 mg of HBTU in acetonitrile was stirred at room temperature for 3.5 hours and then worked-up in the usual manner. The residue was chromatographed on silica gel with a 4: mixture of methylene chloride and methanol as the eluting agent, to obtain 60 mg of N-[(1S,2S.4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]-α-[3-[(2-morpholinoethyl)carbamoyl]-2-(1-naphthylmethyl)propionamido]imidazole-4-propionamide as a foam. MS: 743 (M+H)+.

Workup

  1. customThe residue was chromatographed on silica gel with a 4
  2. additionmixture of methylene chloride and methanol as the eluting agent

Sources & evidence

ORD record
ord-4754506d5b2a4ca09177682acc45d2a0
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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