Diisopropylethylamine → HCID 54404418, compound

HRID 1018693Notes

Reaction equation

HRID 1018693 reaction equation
CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.Cl.[CH3:35][O:36][C:37](=[O:58])[C@@H:38]([CH2:40][C:41]1[CH:46]=[CH:45][C:44]([NH:47][C:48](=[O:57])[C:49]2[C:54]([Cl:55])=[CH:53][CH:52]=[CH:51][C:50]=2[Cl:56])=[CH:43][CH:42]=1)[NH2:39]>CN(C=O)C.O>[CH3:35][O:36][C:37](=[O:58])[C@@H:38]([CH2:40][C:41]1[CH:42]=[CH:43][C:44]([NH:47][C:48](=[O:57])[C:49]2[C:50]([Cl:56])=[CH:51][CH:52]=[CH:53][C:54]=2[Cl:55])=[CH:45][CH:46]=1)[NH2:39]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 131723645HCID 131723645, compound

Product 1

HCID 54404418HCID 54404418, compoundYield 173.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (1S-trans)-[3-(Phenylmethoxy)carbonyl]-1,2,2-trimethylcyclopentane-1-carboxylic acid, 36-F-1, (503.7 mg) in DMF(5 mL) and DIEA(3 mL) was added O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate(731.7 mg) and the reaction stirred at ambient temperature for 1 hour. To the reaction was added 4-[(2,6-dichlorobenzoyl)amino]-D-phenylalanine methyl ester, hydrochloride salt(698.6 mg), 37-B-2, and the reaction stirred for 5 days. The reaction was then diluted with water and extracted with AcOEt. The concentrated extract was purified by flash chromatography on silica gel eluting with methanol in methylene chloride to obtain (1S-trans)-N-[(3-(Phenylmethoxy)carbonyl)-1,2,2-trimethylcyclopentyl)carbonyl]-4-[(2,6-dichlorobenzoyl)amino]-D-phenylalanine methyl ester(1.1024 g). Physical properties as follows: 1H NMR (CDCl3) δ7.82 (1 H), 7.58 (2 H), 7.28 (8 H), 7.05 (2 H), 6.07 (1 H), 5.06 (2 H), 4.74 (1 H), 3.66 (3 H), 3.07 (3 H), 2.05 (3 H), 1.53 (1 H), 1.21 (3 H), 0.90 (3 H), 0.75 (3 H); MS−ESI (m/z): 637([M−H−]); MS−ESI (m/z): 661([M+Na]+).

Workup

  1. stirring37-B-2, and the reaction stirred for 5 days
  2. extractionextracted with AcOEt
  3. extractionThe concentrated extract
  4. customwas purified by flash chromatography on silica gel eluting with methanol in methylene chloride

Sources & evidence

ORD record
ord-d79665d4654a47dfa8fa373ca07d171d
Source dataset
uspto-grants-2002_11
Patent number
US06482849B1

Reaction notes

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