Tetrahydrofuran → Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester

HRID 476801Notes

Reaction equation

HRID 476801 reaction equation
C(N([CH2:6][CH3:7])CC)C.C1(N=C=N[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)CCCCC1.[CH:23]1([CH2:29][C@H:30](NC(=O)[C@H](CC2N(COCC3C=CC=CC=3)C=NC=2)N)[C@@H:31]([OH:46])C2N(COCC3C=CC=CC=3)C=CN=2)CCC[CH2:25][CH2:24]1.N[C@@H:68](CC1CCCCC1)[C@H:69](C1N(COCC2C=CC=CC=2)C=CN=1)[OH:70].O.[OH:93]N1C2C=CC=CC=2N=N1.[O:103]1[CH2:107][CH2:106][CH2:105][CH2:104]1>>[CH3:68][C:69]([O:103][CH2:107][C:106]1[C:18]2[C:17](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:30]([CH2:31][O:46][C:6]([CH3:7])=[O:93])=[C:29]2[C:105]=1[CH:104]=[CH:25][CH:24]=[CH:23]2)=[O:70]

Participants

7

Reactant 6

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 15021503HCID 15021503, compoundHCID 70073167HCID 70073167, compound

Product 1

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester

Procedure

Triethylamine (0.84 ml., 6.0 mmole) and dicyclohexylcarbodiimide (453 mg., 2.20 mmole) are added to mixture of N-[(1S, 2R)-1-(cyclohexylmethy)-2-hydroxy-2-[1-[(phenylmethoxy)methyl]-1H-imidazol-2-yl]ethyl]-N3 -[(phenylmethoxy)methyl]-L-histidinamide (1.47 g., 2.0 mmole) [prepared as set forth in Example 11 (e)], the product from part (c) (582 mg., 2.20 mmole), and 1-hydroxybenzotriazole hydrate (337 mg., 2.20 mmole) in tetrahydrofuran (8 ml.) at 0°. The resulting mixture is stirred overnight as it warms to 25°, after which it is filtered. The filtrate is diluted with ethyl acetate, washed with saturated sodium bicarbinate solution and brine, dried (MgSO4), and concentrated. The residue is flash chromatographed on silica gel (Merck) eluting with ethyl acetate:pyridine:acetic ecid:water (80:20:6:11) to give as the major product 1.48 g. of N-[(S)-2-cyclohexyl-1-[(R)-hydroxy[1-[(phenylmethoxy)methyl]-1H-imidazol-2-yl]methyl]ethyl]-N2 -[N-[[(1,1-dimethylethyl)amino]-carbonyl]-L-phenylalanyl]-N3 -[(phenylmethoxy)methyl]-L-histidinamide. [α]D =-3.5° (c=9, methanol).

Workup

  1. customprepared
  2. customat 0°
  3. customwarms to 25°
  4. filtrationafter which it is filtered
  5. additionThe filtrate is diluted with ethyl acetate
  6. washwashed with saturated sodium bicarbinate solution and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customchromatographed on silica gel (Merck)
  10. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-2769bcbd8a114d6a9b65fbb4ae9e8bd1
Source dataset
uspto-grants-1989_12
Patent number
US04885292

Reaction notes

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