Acetic Acid → HCID 57971654, compound

HRID 2277015Notes

Reaction equation

HRID 2277015 reaction equation
[C:1]([O:5][C:6](=[O:31])[C@@H:7]([NH:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH:19]([CH2:22][NH:23]C(OC(C)(C)C)=O)[CH2:18][CH2:17]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:32]([O:36][CH:37]([O:39][NH:40][C:41]([C:43]1[S:47][C:46]2[CH:48]=[C:49]([CH:52]=O)[CH:50]=[CH:51][C:45]=2[CH:44]=1)=[O:42])[CH3:38])[CH:33]([CH3:35])[CH3:34].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.C(Cl)Cl>[C:1]([O:5][C:6](=[O:31])[C@@H:7]([NH:14][CH2:15][CH:16]1[CH2:17][CH2:18][CH:19]([CH2:22][NH:23][CH2:52][C:49]2[CH:50]=[CH:51][C:45]3[CH:44]=[C:43]([C:41](=[O:42])[NH:40][O:39][CH:37]([O:36][CH2:32][CH:33]([CH3:34])[CH3:35])[CH3:38])[S:47][C:46]=3[CH:48]=2)[CH2:20][CH2:21]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57971603HCID 57971603, compoundHCID 57971713HCID 57971713, compound

Product 1

HCID 57971654HCID 57971654, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

(S)-{[4-(tert-Butoxycarbonylamino-methyl)-cyclohexylmethyl]-amino}-phenyl-acetic acid tert-butyl ester (290 mg, 0.9 mmol) and 6-formyl-benzo[b]thiophene-2-carboxylic acid (1-isobutoxy-ethoxy) amide (Scheme 7) (255 mg, 0.8 mmol) were stirred in DCE (8 ml) for 30 min. Acetic acid (4 ul, 0.08 mmol) and sodium triacetoxyborohydride (504 mg, 2.4 mmol) were added and the reaction mixture was stirred at r.t. for 1 h30. DCM (5 ml) and a saturated solution of NaHCO3 (10 ml) were added and phases were separated. The aqueous phase was extracted with EtOAc (15 ml). The organics were dried over magnesium sulfate, filtered and concentrated under vacuum. The crude product (543 mg) was purified on column chromatography (5 to 10% MeOH in DCM) to yield the expected pure product (172 mg, 34% yield). LCMS purity 100%, m/z 638 [M++H]+.

Workup

  1. customphases were separated
  2. extractionThe aqueous phase was extracted with EtOAc (15 ml)
  3. dry with materialThe organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe crude product (543 mg) was purified on column chromatography (5 to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-15fb61b6c0a74990a0810ef1f70d3be5
Source dataset
uspto-grants-2015_09
Patent number
US09133104B2

Reaction notes

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