tert-butyl N-(2-oxoethyl)carbamate → HCID 86725268, compound

HRID 1478871Notes

Reaction equation

HRID 1478871 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][C:11]([NH:13][CH:14]([B:27]3[O:35][CH:34]4[C:29]([CH3:39])([CH:30]5[CH2:36][CH:32]([CH2:33]4)[C:31]5([CH3:38])[CH3:37])[O:28]3)[CH2:15][C:16]3[C:17]([O:25][CH3:26])=[C:18]([CH:22]=[CH:23][CH:24]=3)[C:19]([OH:21])=[O:20])=[O:12])=[CH:7][CH:8]=2)[CH2:3][NH:2]1.[C:40]([NH:47][CH2:48][CH:49]=O)([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41]>CO>[C:43]([O:42][C:40]([NH:47][CH2:48][CH2:49][N:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[C:6]([CH2:10][C:11]([NH:13][CH:14]([B:27]3[O:35][CH:34]4[C:29]([CH3:39])([CH:30]5[CH2:36][CH:32]([CH2:33]4)[C:31]5([CH3:38])[CH3:37])[O:28]3)[CH2:15][C:16]3[C:17]([O:25][CH3:26])=[C:18]([CH:22]=[CH:23][CH:24]=3)[C:19]([OH:21])=[O:20])=[O:12])[CH:5]=2)[CH2:1]1)=[O:41])([CH3:46])([CH3:45])[CH3:44]

Participants

4

Reactant 2

HCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 86725265HCID 86725265, compound

Product 1

HCID 86725268HCID 86725268, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-[2-(2-2,3-Dihydro-1H-isoindol-5-yl-acetylamino)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)-ethyl]-2-methoxy-benzoic acid (0.110 g, 0.207 mmol) (prepared following the procedures in Steps 1-4 in Example 48), N-Boc-2-aminoacetaldehyde (0.06 g, 0.427 mmol), and methanol (2.5 mL) was purged with argon. Palladium on carbon (10%, 0.051 g) was added, the flask evacuated, and the reaction placed under hydrogen for 91 hr. The reaction mixture was filtered through a Celite-plugged filter frit, washed with CH3OH and CH2Cl2, and concentrated. The crude product was carried forward without purification. ESI-MS m/z 676 (MH)+.

Workup

  1. customwas purged with argon
  2. additionPalladium on carbon (10%, 0.051 g) was added
  3. customthe flask evacuated
  4. filtrationThe reaction mixture was filtered through a Celite-plugged
  5. filtrationfilter frit
  6. washwashed with CH3OH and CH2Cl2
  7. concentrationconcentrated
  8. customThe crude product was carried forward without purification

Sources & evidence

ORD record
ord-2564a2b07a844925a56befd510e9a8fe
Source dataset
uspto-grants-2016_08
Patent number
US09403850B2

Reaction notes

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