Diisopropylethylamine → HCID 131723201, compound

HRID 843402Notes

Reaction equation

HRID 843402 reaction equation
[CH3:1][N:2]([C@H:32]([CH3:37])[C:33]([O:35][CH3:36])=[O:34])[C:3](=[O:31])[CH:4]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=2)=[CH:11][CH:10]=1)[CH2:5][C:6]([OH:8])=O.Cl.CN.C[CH2:42][N:43](C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.CCOC(C)=O>[CH3:1][N:2]([C@H:32]([CH3:37])[C:33]([O:35][CH3:36])=[O:34])[C:3](=[O:31])[CH:4]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[C:21]([C:23]([F:25])([F:26])[F:24])[CH:20]=[C:19]([C:27]([F:28])([F:29])[F:30])[CH:18]=2)=[CH:11][CH:10]=1)[CH2:5][C:6]([NH:43][CH3:42])=[O:8]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 6364545Methylamine hydrochlorideHCID 131723200HCID 131723200, compound

Product 1

HCID 131723201HCID 131723201, compoundYield 101.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 2-{N-methyl-N-[(R/S)-α-hydroxycarbonylmethyl-4-(3,5-bistrifluoromethylbenzyloxy)phenylacetyl]amino}-(R)-propionate 48f (0.3 g, 0.56 mmol), methylamine hydrochloride (68 mg, 1 mmol) and DIEA (0.35 mL, 2 mmol) in DMF (5 mL) was cooled in an ice bath and to it was added BOP (265 mg, 0.6 mmol). After stirring at room temperature for 1 hour, EtOAc was added and the solution was washed with NaHCO3 and brine, dried over MgSO4, and concentrated to give the amide (312 mg, 100%) as a solid. MS (ESI): (M+Na)+=571.8.

Workup

  1. washthe solution was washed with NaHCO3 and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a097d24b70e04f8cb3f5f15550adcfdd
Source dataset
uspto-grants-2002_04
Patent number
US06376665B1

Reaction notes

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