Triethylamine → HCID 59304969, compound

HRID 254772Notes

Reaction equation

HRID 254772 reaction equation
C(OC([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[N:24][C:23]([NH:26][CH2:27][C:28]3[CH:37]=[CH:36][C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH:29]=3)=[CH:22][N:21]=2)=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=O)(C)(C)C.O[CH2:39][CH2:40][N:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1.C(N(CC)CC)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>ClCCl>[NH2:8][C@@H:9]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:25]=[N:24][C:23]([NH:26][CH2:27][C:28]3[CH:37]=[CH:36][C:31]4[C:30](=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH:29]=3)=[CH:22][N:21]=2)=[CH:18][CH:19]=1)[C:10]([O:12][CH2:39][CH2:40][N:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1)=[O:11]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 611632-MorpholinoethanolHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate2×HCID 59304962HCID 59304962, compound

Product 1

HCID 59304969HCID 59304969, compoundYield 4.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-2-(Tert-butoxycarbonylamino)-3-(4-(5-(naphthalen-2-ylmethylamino)pyrazin-2-yl)phenyl)propanoic acid (48 mg, 0.090 mmol), 4-(2-hydroxyethyl)morpholine (12 mg, 0.090 mmol), triethylamine (18 mg, 0.180 mmol), and benzotriazole-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate (BOP, 18 mg, 0.090 mmol), in dichloromethane (3.0 ml) were stirred at room temperature for 5 hours. Additional triethylamine (18 mg, 0.180 mmol) and BOP (18 mg, 0.090 mmol) were added, and the mixture was stirred overnight. The mixture was concentrated and purified via prep HPLC to give 2 mg of the captioned compound.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified via prep HPLC

Sources & evidence

ORD record
ord-11bf49803ec240a08b82e645a32d4f4d
Source dataset
uspto-grants-2011_01
Patent number
US07875622B2

Reaction notes

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