Aniline → HCID 20592410, compound

HRID 1368959Notes

Reaction equation

HRID 1368959 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:13]([NH:15][CH:16]([CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH:17]([C:19]1[O:20][CH:21]=[C:22]([C:24](O)=[O:25])[N:23]=1)[OH:18])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CN([P+](ON2N=[N:63][C:58]3[CH:59]=[CH:60][CH:61]=[CH:62][C:57]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.NC1C=CC=CC=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[CH3:37][CH:36]([CH3:38])[CH2:35][CH:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:13](=[O:14])[NH:15][CH:16]([CH2:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH:17]([OH:18])[C:19]1[O:20][CH:21]=[C:22]([C:24](=[O:25])[NH:63][C:58]2[CH:57]=[CH:62][CH:61]=[CH:60][CH:59]=2)[N:23]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 18517793HCID 18517793, compound

Product 1

HCID 20592410HCID 20592410, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution comprised of 2-[2-(2-benzyloxycarbonylamino-4-methylvalerylamino)-1-hydroxy-4-phenylbutyl]oxazole-4-carboxylic acid (0.05 g, 0.096 mmol), provided as in Example 7, in DMF (5 mL) was stirred while PyBOP® (0.05 g, 0.096 mmol) and aniline (9 mg, 0.096 mmol) were added. The mixture was stirred for an additional 2 minutes and diisopropylethylamine (12.4 mg, 0.096 mmol) was added. The mixture was stirred for 2 hours at room temperature, poured into cold water 0° C. at and extracted with ethyl acetate (4×30 mL). The extracts were combined, dried (MgSO4) and then concentrated. The product was purified from the residue by flash chromatography eluting with 1:2 hexanes/ethyl acetate to provide benzyl 3-methyl-1-[2-hydroxy-1-phenethyl-2-(4-phenylcarbamoyloxazol-2-yl)ethylcarbamoyl]butylcarbamate (30 mg, 0.05 mmol) as a white solid. MS (ESI)) m/z=599 (M+1); 1H NMR (CDCl3): δ 0.8-1.05 (d, J=4 Hz, 6H), 1.35 (m, 1H), δ 1.55 (m, 1H), δ 2.00-2.15 (m, 2H), δ 2.62 (m, 2H), δ 2.80 (m, 2H), δ 3.65 (m, 2H), δ 4.11 (m, 1H1), δ 4.30 (m, 1H), δ 4.45 (m, 1H), δ 4.95 (s, 1H) 5.17 (s, 2H), δ 5.2 (d, J=4 Hz, 1H), δ 6.70 (d, J=5 Hz 1H), δ 7.1-7.45 (m, 15H) 7.7(d, J=4 Hz, 1H), δ 8.19 (s, 1H), δ 8.99 (s, 1H), (C34H38N4O6).

Workup

  1. additionwere added
  2. stirringThe mixture was stirred for 2 hours at room temperature
  3. extractionextracted with ethyl acetate (4×30 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe product was purified from the residue by flash chromatography
  7. washeluting with 1:2 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-b77fe4f0a0ef4a54b01b0915839d3359
Source dataset
uspto-grants-2003_06
Patent number
US06576630B1

Reaction notes

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